GB762068A - A novel alcohol and a process for the manufacture thereof - Google Patents

A novel alcohol and a process for the manufacture thereof

Info

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
Application number
GB8259/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Roche Products Ltd filed Critical Roche Products Ltd
Publication of GB762068A publication Critical patent/GB762068A/en
Expired legal-status Critical Current

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.
GB8259/56A 1953-07-07 1954-07-07 A novel alcohol and a process for the manufacture thereof Expired GB762068A (en)

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)

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