GB762068A - A novel alcohol and a process for the manufacture thereof - Google Patents
A novel alcohol and a process for the manufacture thereofInfo
- Publication number
- GB762068A GB762068A GB8259/56A GB825956A GB762068A GB 762068 A GB762068 A GB 762068A GB 8259/56 A GB8259/56 A GB 8259/56A GB 825956 A GB825956 A GB 825956A GB 762068 A GB762068 A GB 762068A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexen
- methyl
- trimethyl
- lower alkyl
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises a novel alcohol 4-methyl - 6 - [21.61.61 - trimethyl - cyclohexen-(11) - yl] - hexadien - (2.4) - ol - (1). It may be prepared by condensing 2-methyl-4-[21.61.61-trimethyl - cyclohexen - (11) - yl] - buten - (2)-al-(1) with a halogeno-acetic acid lower alkyl ester and either dehydrating the resulting 2.3-epoxy - 4 - methyl - 6 - [21.61.61 - trymethyl-cyclohexen - (11 - yl] - hexen - (4) - oic - (1) - acid lower alkyl ester or 3-hydroxy-4-methyl-6-[21.61.61 - trimethyl - cyclohexen - (11) - yl]-(11) - yl] - hexen - (4) - oic - (1) - acid lower alkyl ester by heating in a solvent in the presence of an acidic dehydrating agent and then reducing the resulting lower alkyl esters of 4-methyl-6-[21.61.61 - trimethyl - cyclohexen - (11) - yl]-hexadien - (2.4) oic - (1) - acid with lithium aluminium hydride or reducing the said 3-hydroxy or 3-epoxy compound with lithium aluminium hydride and then dehydrating the so-formed 4 - methyl - 6 - [21.61.61 - trimethyl-cyclohexen - (11) - yl] - hexen - (4) - diol - (1.3) by heating with an acidic dehydrating agent after initially esterifying the primary hydroxy group. The " lower alkyl " groups referred to are those alkyl groups containing not more than 4 carbon atoms. When the epoxy ester is formed in the first step it may be heated to form the corresponding keto-acid ester which may then be reduced to the corresponding hydroxy ester. The condensation may be brought about using ethyl bromoacetate or chloroacetate in the presence of a metal, e.g. zinc, or an alkali metal alcoholate, e.g. sodium methylate, as condensing agent. A suitable acidic dehydrating agent is, for example, p-toluene sulphonic acid. Specification 762,067 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH762068X | 1953-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB762068A true GB762068A (en) | 1956-11-21 |
Family
ID=4534760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8259/56A Expired GB762068A (en) | 1953-07-07 | 1954-07-07 | A novel alcohol and a process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB762068A (en) |
-
1954
- 1954-07-07 GB GB8259/56A patent/GB762068A/en not_active Expired
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