US2838576A - Tertiary alcohols - Google Patents
Tertiary alcohols Download PDFInfo
- Publication number
- US2838576A US2838576A US2838576DA US2838576A US 2838576 A US2838576 A US 2838576A US 2838576D A US2838576D A US 2838576DA US 2838576 A US2838576 A US 2838576A
- Authority
- US
- United States
- Prior art keywords
- ethylenic
- magnesium
- solution
- general formula
- tertiary alcohols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000003509 tertiary alcohols Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000002734 organomagnesium group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- -1 gums Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- PHMRPWPDDRGGGF-UHFFFAOYSA-N 2-bromoprop-1-ene Chemical compound CC(Br)=C PHMRPWPDDRGGGF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/28—Metal alcoholates
Definitions
- a perfumery base material as used herein is meant a material or a mixture of materials which serves as a vehicle for odiferous compounds in the art of perfumery or cosmetics.
- the material or mixture of materials may, as in the perfumery art, serve merely to render the odiferous compounds convenient to handle and permit them to exhibit their properties advantageously or it may, as in the cosmetic art, have desirable properties of its own and be used as a vehicle for odiferous substances in order to render it more attractive for personal use.
- a perfumery base material used in perfumery may for example be ethyl alcohol or a concentrated aqueous solution thereof such as a solution of 80% by weight concentration.
- perfumery base materials may take the form of cold creams, hand lotions, hand creams, vanishing creams, face powders, face rouges, lipsticks, shampoos, hair oils, hair creams etc., compounded according to the methods and formulae well understood in the art from such products as waxes such as beeswax, or spermaceti, oils such as castor oil, mineral oils or lanolin, soaps, glycerine, surface active agents, gums, talc, chalk, kaolin, Water repellants such as zinc stearate, pigments, dyes and gums such as gum tragacanth.
- the perfumery base material may have compounded therein other odiferous substances of synthetic or animal or vegetable origin in addition to one or more of the new compounds provided by the invention for the purpose of producing composite odour
- the invention also includes within its scope a new process for the preparation of the alcohols of general Forests Patent O 2,838,576 Patented June 10,
- the ethylenic organo-magnesium derivative is preferably employed in excess and the complex is preferably decomprsed with a cold aqueous solution of ammonium chlon e.
- the invention fu rther includes within its scope a modification of the said new process which can be applied to the preparation, of certain .known-diethylenic alcohols, for example linalool, in which modifications each one of the symbols R R and R represents a hydrogen atom.
- the ethylenic organo-magnesium derivatives of Formula III can conveniently be prepared by reacting magnesium with a solution, in tetrahydrofuran, of an ethylenic compound of the general formula:
- Example Magnesium (24 g.) is introduced into dry tetrahydrofuran (200 cc.) containing a trace of iodine and then a solution of vinyl bromide (107 g.) in an equal weight of tetrahydrofuran is added to it, drop by drop, with stirring.
- the magnesium solution thus obtained is cooled in ice.
- a solution of 2-methyl-hept-2-en-6-one (101 g.) in an equal volume of anhydrous ether is then added with vigorous stirring. When the addition is complete, the mixture is stirred for a further hour and then allowed to stand for 12 hours. ammonium chloride is then added to decompose the magnesium complex formed.
- the mixture separates into two layers; the organic layer is decanted and dried over anhydrous potassium carbonate, freed from solvents by heating on a water bath, and then rectified by distillation under reduced pressure.
- dl-linalool (103 g.) of good purity, representing a yield of 83%, separates at 83 to 85 C. under a pressure of 12.5 mm. of mercury.
- a process for the preparation of diethylenic alcohols which comprises reacting magnesium with a solution in tetrahydrofuran of an ethylenic compound of the general formula:
- R R and R are each selected from the class consisting of hydrogen atoms and alkyl groups of from 1 to 5 carbon atoms, condensing the ethylenic organo-magnesium derivative thus obtained with a 'y-ethylenic ketone of the general formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
TERTIARY ALCOHOLS Henri Normant, Paris, France, assignor to Societe des Usines Chimiques Rhone-Poulenc, Paris, France, a French body corporate No Drawing. Application January 27, 1956 Serial No. 561,928
Claims priority, application France February 3, 1955 2 Claims. (Cl. 260- 638 in which the symbols R and R each represent a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms or an aryl group, the symbol R represents a hydrogen atom or a methyl group, and the symbols R R and R each represent a hydrogen atom or an alkyl group containing from 1 to 5 carbon atoms, one at least of the symbols R R and R representing an alkyl group. These new compounds have agreeable bergamot-lavender odours each with its own particular shade. They are accordingly useful in perfumery and the invention includes within its scope a perfume composition containing at least one diethylenic alcohol of the general Formula I.
By the expression a perfumery base material as used herein is meant a material or a mixture of materials which serves as a vehicle for odiferous compounds in the art of perfumery or cosmetics. The material or mixture of materials may, as in the perfumery art, serve merely to render the odiferous compounds convenient to handle and permit them to exhibit their properties advantageously or it may, as in the cosmetic art, have desirable properties of its own and be used as a vehicle for odiferous substances in order to render it more attractive for personal use. A perfumery base material used in perfumery may for example be ethyl alcohol or a concentrated aqueous solution thereof such as a solution of 80% by weight concentration. It may contain such additives as gums, balsams and oleo-resins for retarding its rate of evaporation. Other perfumery base materials may take the form of cold creams, hand lotions, hand creams, vanishing creams, face powders, face rouges, lipsticks, shampoos, hair oils, hair creams etc., compounded according to the methods and formulae well understood in the art from such products as waxes such as beeswax, or spermaceti, oils such as castor oil, mineral oils or lanolin, soaps, glycerine, surface active agents, gums, talc, chalk, kaolin, Water repellants such as zinc stearate, pigments, dyes and gums such as gum tragacanth. As will be understood by those skilled in the art the perfumery base material may have compounded therein other odiferous substances of synthetic or animal or vegetable origin in addition to one or more of the new compounds provided by the invention for the purpose of producing composite odours.
The invention also includes within its scope a new process for the preparation of the alcohols of general Forests Patent O 2,838,576 Patented June 10,
mula I. This process consists in condensing a 'y-ethylenic ketone of the general formula:
C=C-OHzCHgCOCH; II R; R3
with an ethylenic organo-magnesium derivative of the general formula:
R5 R /C XMg( 3 a in which general formulae the symbols R R R R R and R are as hereinbefore defined and the symbol X represents a halogen atom (preferably bromine), and then decomposing the complex obtained with water. The ethylenic organo-magnesium derivative ispreferably employed in excess and the complex is preferably decomprsed with a cold aqueous solution of ammonium chlon e.
The invention fu rther includes within its scope a modification of the said new process which can be applied to the preparation, of certain .known-diethylenic alcohols, for example linalool, in which modifications each one of the symbols R R and R represents a hydrogen atom.
The ethylenic organo-magnesium derivatives of Formula III can conveniently be prepared by reacting magnesium with a solution, in tetrahydrofuran, of an ethylenic compound of the general formula:
III
The advantage of the aforesaid process over the previously known process is evident from its application to the preparation of dl-linalool described in the first part of the example which follows. The synthesis of dl-lina- 1001 was carried out by Ruzicka and Fornasir, Helv. Chim. Acta, 2, 184 (1919), by adding a molecule of acetylene to a molecule of 2-methyl-l1ept-2-en-6-one and transforming the acetylenic triple bond of the reaction product into an ethylenic double bond by cautious hydrogenation. The process according to the invention permits the synthesis of dl-linalool in a single operation with an excellent yield.
The following example illustrates the process of the invention.
Example Magnesium (24 g.) is introduced into dry tetrahydrofuran (200 cc.) containing a trace of iodine and then a solution of vinyl bromide (107 g.) in an equal weight of tetrahydrofuran is added to it, drop by drop, with stirring. The magnesium solution thus obtained is cooled in ice. A solution of 2-methyl-hept-2-en-6-one (101 g.) in an equal volume of anhydrous ether is then added with vigorous stirring. When the addition is complete, the mixture is stirred for a further hour and then allowed to stand for 12 hours. ammonium chloride is then added to decompose the magnesium complex formed. The mixture separates into two layers; the organic layer is decanted and dried over anhydrous potassium carbonate, freed from solvents by heating on a water bath, and then rectified by distillation under reduced pressure. dl-linalool (103 g.) of good purity, representing a yield of 83%, separates at 83 to 85 C. under a pressure of 12.5 mm. of mercury.
By following the same procedure, there are also obtained with comparable yields the following new compounds which exhibited an agreeable bergamot-lavender odour in various shades:
Commencing with l-bromopropene, 2:6-dimethyl-nona- A saturated aqueous solution of p 3 2:7 dien 6 01, B. P. =99-100 C.; 11 :0864; n =1.4652.
Commencing with l-bromo-hept-l-ene, 2:6-dimethyltrideca-2z7-dien-6-ol, B. P. =154-156 C.; d =O.842; n =1.4661.
Commencing with l-bromoisobutene, 2:6:8-trimethylnona-2z7-dien-6-ol; B. P. =106l07 C.; 11 :0866; n =1.4692.
Commencing with 2-bromopropene, 2:6:7-trimethylocza 2:7 dien 6 01, B. P. =98-99 C.; 11 :0366; n =1.4658.
I claim:
1. A process for the preparation of diethylenic alcohols which comprises reacting magnesium with a solution in tetrahydrofuran of an ethylenic compound of the general formula:
wherein X is a halogen atom and R R and R are each selected from the class consisting of hydrogen atoms and alkyl groups of from 1 to 5 carbon atoms, condensing the ethylenic organo-magnesium derivative thus obtained with a 'y-ethylenic ketone of the general formula:
References Cited in the file of this patent UNITED STATES PATENTS 2,589,275 Naves Mar. 18, 1952 FOREIGN PATENTS 544,388 Germany Feb. 19, 1932 OTHER REFERENCES Krestinsky: Berichte d. d. c. Ges., vol. B (1922), pps. 2762-3.
Beilstein, Band I (first supplement), p. 240 (1928).
Naves Etudes Bull. Soc. Chim. (France) p. 507, table (1951).
Lewis et al.: I. A. C. 8., vol. 74 (1952), pps. 12537.
Claims (1)
1. A PROCESS FOR THE PREPARATION OF DIETHYLENIC ALCOHOLS WHICH COMPRISES REACTING MAGNESIUM WITH A SOLUTION IN TETRAHYDROFURAN OF AN ETHYLENIC COMPOUND OF THE GENERAL FORMULA:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2838576A true US2838576A (en) | 1958-06-10 |
Family
ID=3447109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2838576D Expired - Lifetime US2838576A (en) | Tertiary alcohols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2838576A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3296080A (en) * | 1963-08-08 | 1967-01-03 | Rhodia | Linalool homologues |
| US3452105A (en) * | 1963-10-25 | 1969-06-24 | Givaudan Corp | 3-hydroxy-7-isobutyl-1,6-octadiene |
| US4198532A (en) * | 1977-08-04 | 1980-04-15 | Givaudan Corporation | Novel alcohol odorants |
| US4375005A (en) * | 1981-11-19 | 1983-02-22 | International Flavors & Fragrances Inc. | Branched chain olefinic alcohols, thiols, esters and ethers, organoleptic uses thereof, processes for preparing same and intermediates therefor |
| US4560499A (en) * | 1982-05-20 | 1985-12-24 | International Flavors & Fragrances Inc. | Isosolanone and solanone intermediates and organoleptic uses |
| US5091598A (en) * | 1987-12-30 | 1992-02-25 | Societe Nationale Elf Aquitaine | Manufacture of tertiary and secondary alcohols by the action of an organic halogen compound and manganese on a compound carrying a carbonyl group |
| US6492567B1 (en) * | 2001-10-24 | 2002-12-10 | Council Or Scientific And Industrial Research | Dihydrotagetone alcohol and a method for preparation thereof from Tagetes minuta oil |
| WO2014095321A1 (en) | 2012-12-20 | 2014-06-26 | Firmenich Sa | Sage odorant |
| WO2015169648A1 (en) * | 2014-05-08 | 2015-11-12 | Firmenich Sa | Floral, green odorant |
| JP2015537064A (en) * | 2012-10-08 | 2015-12-24 | ディーエスエム アイピー アセッツ ビー．ブイ． | Flavor flavor compound (IV) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE544388C (en) * | 1930-09-25 | 1932-02-19 | I G Farbenindustrie Akt Ges | Process for the production of unsaturated carbinols |
| US2589275A (en) * | 1948-02-04 | 1952-03-18 | Givaudan Corp | Preparation of 3-methyl-citrals |
-
0
- US US2838576D patent/US2838576A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE544388C (en) * | 1930-09-25 | 1932-02-19 | I G Farbenindustrie Akt Ges | Process for the production of unsaturated carbinols |
| US2589275A (en) * | 1948-02-04 | 1952-03-18 | Givaudan Corp | Preparation of 3-methyl-citrals |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3296080A (en) * | 1963-08-08 | 1967-01-03 | Rhodia | Linalool homologues |
| US3452105A (en) * | 1963-10-25 | 1969-06-24 | Givaudan Corp | 3-hydroxy-7-isobutyl-1,6-octadiene |
| US4198532A (en) * | 1977-08-04 | 1980-04-15 | Givaudan Corporation | Novel alcohol odorants |
| US4375005A (en) * | 1981-11-19 | 1983-02-22 | International Flavors & Fragrances Inc. | Branched chain olefinic alcohols, thiols, esters and ethers, organoleptic uses thereof, processes for preparing same and intermediates therefor |
| US4560499A (en) * | 1982-05-20 | 1985-12-24 | International Flavors & Fragrances Inc. | Isosolanone and solanone intermediates and organoleptic uses |
| US5091598A (en) * | 1987-12-30 | 1992-02-25 | Societe Nationale Elf Aquitaine | Manufacture of tertiary and secondary alcohols by the action of an organic halogen compound and manganese on a compound carrying a carbonyl group |
| US6492567B1 (en) * | 2001-10-24 | 2002-12-10 | Council Or Scientific And Industrial Research | Dihydrotagetone alcohol and a method for preparation thereof from Tagetes minuta oil |
| JP2015537064A (en) * | 2012-10-08 | 2015-12-24 | ディーエスエム アイピー アセッツ ビー．ブイ． | Flavor flavor compound (IV) |
| CN104837798A (en) * | 2012-12-20 | 2015-08-12 | 弗门尼舍有限公司 | Sage odorant |
| WO2014095321A1 (en) | 2012-12-20 | 2014-06-26 | Firmenich Sa | Sage odorant |
| JP2016506435A (en) * | 2012-12-20 | 2016-03-03 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | Sage odor substance |
| US9284513B2 (en) | 2012-12-20 | 2016-03-15 | Firmenich Sa | Sage odorant |
| CN104837798B (en) * | 2012-12-20 | 2017-05-17 | 弗门尼舍有限公司 | Sage odorant |
| WO2015169648A1 (en) * | 2014-05-08 | 2015-11-12 | Firmenich Sa | Floral, green odorant |
| CN106456473A (en) * | 2014-05-08 | 2017-02-22 | 弗门尼舍有限公司 | Floral, green odorant |
| US20170145342A1 (en) * | 2014-05-08 | 2017-05-25 | Firmenich Sa | Floral, green odorant |
| JP2017514979A (en) * | 2014-05-08 | 2017-06-08 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | Floral, green odor substance |
| US9758744B2 (en) * | 2014-05-08 | 2017-09-12 | Firmenich Sa | Floral, green odorant |
| CN106456473B (en) * | 2014-05-08 | 2020-04-03 | 弗门尼舍有限公司 | Floral and green scent agent |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3773836A (en) | Indanone derivatives and processes for producing same | |
| Pauling et al. | The Rearrangement of α‐Acetylenic Alcohols to α, β‐Unsaturated Carbonyl Compounds by Silylvanadate Catalysts | |
| US2838576A (en) | Tertiary alcohols | |
| US3296080A (en) | Linalool homologues | |
| US3636113A (en) | Novel fragrance materials chemical intermediates and processes | |
| US3927083A (en) | Bicyclic compounds and processes for making and using same | |
| US3669908A (en) | Alkadienyl pyridines and pyrazines as perfumes | |
| US3716498A (en) | Novel fragrance compositions | |
| House et al. | Synthesis of Δ8, 9-and Δ9, 10-Octal-1-one1 | |
| US3660311A (en) | Novel fragrance methods and compositions | |
| US3678119A (en) | Acid isomerization of chamigrenes | |
| US3996169A (en) | Perfume uses of tricyclic alcohols and processes | |
| Jones et al. | 210. Researches on acetylenic compounds. Part LX. The synthesis of three natural polyacetylenic hydrocarbons | |
| US3876561A (en) | Novel odorant cyclododecyl ethers | |
| US3417132A (en) | 4,7-methanoindene derivatives | |
| US4119575A (en) | Polycyclic alcohol perfume compositions | |
| US3966648A (en) | 2-Alkyl-oct-5-en-2-ols in fragrance compositions | |
| US3845141A (en) | Cyclododecyl ethers | |
| US3991123A (en) | Tetracyclic alcohols | |
| US2293775A (en) | Para tolylethyl acetate | |
| GB777515A (en) | Improvements in or relating to tertiary alcohols | |
| NO124925B (en) | ||
| US3729514A (en) | Novel chemical compounds and process | |
| JPH01156932A (en) | Tricyclo (6, 2, 1, 01'6) undecanes and production thereof | |
| US3876562A (en) | 7,7a-epoxy-5,6,7a-tetrahydro-1,1,2,3,3-pentamethyl 4(3ah)-indanone perfume composition |