GB633711A - Improvements in or relating to the production of compounds containing the isoprene grouping - Google Patents

Improvements in or relating to the production of compounds containing the isoprene grouping

Info

Publication number
GB633711A
GB633711A GB37847/46A GB3784746A GB633711A GB 633711 A GB633711 A GB 633711A GB 37847/46 A GB37847/46 A GB 37847/46A GB 3784746 A GB3784746 A GB 3784746A GB 633711 A GB633711 A GB 633711A
Authority
GB
United Kingdom
Prior art keywords
acetone
magnesium
ionone
dehydration
isoprene
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
GB37847/46A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB37847/46A priority Critical patent/GB633711A/en
Publication of GB633711A publication Critical patent/GB633711A/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
    • C07C403/14—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 doubly-bound oxygen atoms
    • C07C403/16—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 doubly-bound oxygen atoms not being part of —CHO 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
    • C07C403/20—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
    • 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

An isoprene unit is added to an aldehyde or ketone, containing at least three carbon atoms in the molecule, by subjecting said compound successively to a series of four reactions, namely, a condensation with a haloacetate in the presence of zinc or magnesium, a dehydration, a reduction with an aluminium containing hydride and an oxidation in the presence of acetone and an aluminium alkoxide or magnesium alkoxide. Among the compounds specified as starting materials are benzaldehyde, furfural, acetone, diethyl ketone and acetophenone. There may be used as catalysts in the dehydration step, zinc chloride, p-toluene sulphonic acid, iodine, phosphorous oxychloride, oxalyl chloride, phosphorous trichloride and dimethyl aniline hydriodide. The reduction step may be carried out in the presence of a solvent such as ether or dioxane. Detailed examples are given of the process above, starting with (1) b -ionone; (2) allyl acetone; (3) propionaldehyde; (4) hexahydro-pseudo ionone. The products of (1) and (4) are Vitamin A and phytol respectively. Specifications 633,748 and 633,749 are referred to.
GB37847/46A 1946-12-24 1946-12-24 Improvements in or relating to the production of compounds containing the isoprene grouping Expired GB633711A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB37847/46A GB633711A (en) 1946-12-24 1946-12-24 Improvements in or relating to the production of compounds containing the isoprene grouping

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB37847/46A GB633711A (en) 1946-12-24 1946-12-24 Improvements in or relating to the production of compounds containing the isoprene grouping

Publications (1)

Publication Number Publication Date
GB633711A true GB633711A (en) 1949-12-19

Family

ID=10399421

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37847/46A Expired GB633711A (en) 1946-12-24 1946-12-24 Improvements in or relating to the production of compounds containing the isoprene grouping

Country Status (1)

Country Link
GB (1) GB633711A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE946895C (en) * 1953-07-07 1956-08-09 Hoffmann La Roche Process for the preparation of the 8- [2 ', 6', 6'-trimethylcyclohexen- (1 ') - yl] -2, 6-dimethyloctatriene- (2, 4, 6) -as- (1)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE946895C (en) * 1953-07-07 1956-08-09 Hoffmann La Roche Process for the preparation of the 8- [2 ', 6', 6'-trimethylcyclohexen- (1 ') - yl] -2, 6-dimethyloctatriene- (2, 4, 6) -as- (1)

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