GB629414A - A process for the manufacture of pentaenes - Google Patents

A process for the manufacture of pentaenes

Info

Publication number
GB629414A
GB629414A GB5529/47A GB552947A GB629414A GB 629414 A GB629414 A GB 629414A GB 5529/47 A GB5529/47 A GB 5529/47A GB 552947 A GB552947 A GB 552947A GB 629414 A GB629414 A GB 629414A
Authority
GB
United Kingdom
Prior art keywords
pentaenes
yne
dihydroxy
dimethyl
methyl
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
GB5529/47A
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 GB629414A publication Critical patent/GB629414A/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
    • C07C403/06—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
    • 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
    • C07C403/12—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 esterified 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Pentaenes are obtained by condensing by means of a Grignard reaction, b -ionone with 3 - hydroxy - 3 - methyl - hexene - (1) - yne - (5), adding to the triple bond of the 3.7-dihydroxy-3.7 - dimethyl - 9 - (21.61.61 - trimethylcyclohexene - (11) - yl) - nonadiene - 1.8 - yne - (5) so obtained 1 mol. of hydrogen by catalytic hydrogenation, subjecting the resulting 3.7-dihydroxy - 3.7 - dimethyl - 9 - (21,61,61 - tri methyl - cyclohexene - (11) - yl) - nonatorine-(1,5,8) to a re-arrangement and dehydration by the action of an organic acylation agent, e.g. acetic anhydride in the presence of an alkali metal acetate, preferably in the presence of a diluent. Detailed examples are given.
GB5529/47A 1946-02-27 1947-02-26 A process for the manufacture of pentaenes Expired GB629414A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH629414X 1946-02-27

Publications (1)

Publication Number Publication Date
GB629414A true GB629414A (en) 1949-09-20

Family

ID=4524638

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5529/47A Expired GB629414A (en) 1946-02-27 1947-02-26 A process for the manufacture of pentaenes

Country Status (1)

Country Link
GB (1) GB629414A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1005956B (en) * 1954-12-22 1957-04-11 Hoffmann La Roche Process for the production of vitamin A or its esters
DE1028118B (en) * 1951-09-11 1958-04-17 Eastman Kodak Co Process for the production of vitamin A aldehyde, alcohol or its esters
EP1031561A1 (en) * 1999-02-22 2000-08-30 F. Hoffmann-La Roche Ag Manufacture of cycloalkenylpolyene esters

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1028118B (en) * 1951-09-11 1958-04-17 Eastman Kodak Co Process for the production of vitamin A aldehyde, alcohol or its esters
DE1005956B (en) * 1954-12-22 1957-04-11 Hoffmann La Roche Process for the production of vitamin A or its esters
EP1031561A1 (en) * 1999-02-22 2000-08-30 F. Hoffmann-La Roche Ag Manufacture of cycloalkenylpolyene esters
US6215009B1 (en) 1999-02-22 2001-04-10 Roche Vitamins Inc. Manufacture of cycloalkenylpolyene esters

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