JPS5640633A - Preparation of gamma-damascone - Google Patents
Preparation of gamma-damasconeInfo
- Publication number
- JPS5640633A JPS5640633A JP11598079A JP11598079A JPS5640633A JP S5640633 A JPS5640633 A JP S5640633A JP 11598079 A JP11598079 A JP 11598079A JP 11598079 A JP11598079 A JP 11598079A JP S5640633 A JPS5640633 A JP S5640633A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methylene
- dimethyl
- carboxylic acid
- acid ester
- 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.)
- Granted
Links
- IXLLBXDECOMIBP-FNORWQNLSA-N (e)-1-(2,2-dimethyl-6-methylidenecyclohexyl)but-2-en-1-one Chemical compound C\C=C\C(=O)C1C(=C)CCCC1(C)C IXLLBXDECOMIBP-FNORWQNLSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- -1 salt compound Chemical class 0.000 abstract 2
- JOJUNSZLWDEVCI-UHFFFAOYSA-N 2,2-dimethyl-6-methylidenecyclohexane-1-carboxylic acid Chemical compound CC1(C)CCCC(=C)C1C(O)=O JOJUNSZLWDEVCI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 241000220317 Rosa Species 0.000 abstract 1
- 238000007239 Wittig reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- VCPPTNDHEILJHD-UHFFFAOYSA-N lithium;prop-1-ene Chemical compound [Li+].[CH2-]C=C VCPPTNDHEILJHD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as a rose perfumery, in a short step and in high yield, from an intermediate obtained by subjecting a 3,3-dimethyl-1- cyclohexanone-2-carboxylic acid ester to Wittig reaction, thereby selectively methylating the ketone group attached to the ring.
CONSTITUTION: 3,3-Dimethyl-1-cyclohexanone-2-carboxylic acid ester of formula I (R is alkyl) is reacted with a Wittig reagent of a methylenylide, pref. methylene triphenylphosphinylide to obtain 2-methylene-6,6-dimethylcyclohexane-carboxylic acid ester of formula II, which is made to react with an allyl metal salt compound, pref. allyl lithium to afford 1-buten-4-one-1-(2-methylene-6,6-dimethyl-cyclohexane) of formula III. The objective compound of formula IV is prepared by the isomerization of the compound of formula III in the presence of a base such as potassium alkoxide, etc.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11598079A JPS5819658B2 (en) | 1979-09-10 | 1979-09-10 | Production method of γ-damascone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11598079A JPS5819658B2 (en) | 1979-09-10 | 1979-09-10 | Production method of γ-damascone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5640633A true JPS5640633A (en) | 1981-04-16 |
| JPS5819658B2 JPS5819658B2 (en) | 1983-04-19 |
Family
ID=14675888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11598079A Expired JPS5819658B2 (en) | 1979-09-10 | 1979-09-10 | Production method of γ-damascone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5819658B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378825A2 (en) * | 1989-01-18 | 1990-07-25 | Firmenich Sa | Alicyclic esters and their use as flavouring agents |
-
1979
- 1979-09-10 JP JP11598079A patent/JPS5819658B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378825A2 (en) * | 1989-01-18 | 1990-07-25 | Firmenich Sa | Alicyclic esters and their use as flavouring agents |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5819658B2 (en) | 1983-04-19 |
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