GB745045A - Improvements in methods of manufacturing -a-ionylidene ethanol and -a-ionylidene acetaldehyde - Google Patents

Improvements in methods of manufacturing -a-ionylidene ethanol and -a-ionylidene acetaldehyde

Info

Publication number
GB745045A
GB745045A GB9243/52A GB924352A GB745045A GB 745045 A GB745045 A GB 745045A GB 9243/52 A GB9243/52 A GB 9243/52A GB 924352 A GB924352 A GB 924352A GB 745045 A GB745045 A GB 745045A
Authority
GB
United Kingdom
Prior art keywords
ionylidene
ethanol
ionone
acetonitrile
give
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
GB9243/52A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB745045A publication Critical patent/GB745045A/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
    • 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
    • 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

b -Ionylidene ethanol is made by condensing b -ionone with cyanoacetic acid or an ester thereof; decarboxylating the product, optionally after saponification of the b -ionylidene cyanoacetic ester; saponifying the resulting b -ionylidene acetonitrile to form b -ionylidene acetic acid and reducing this compound, or the derivative obtained by esterifying the same, by means of lithium aluminium hydride, lithium borohydride, sodium borohydride or magnesium-aluminium hydride. The condensation between b -ionone and cyanoacetic acid or its ester is suitably carried out under azeotropic distillation with benzene using a water trap. In a preferred modification of the invention, the b -ionylidene ethanol obtained by the above process is oxidized with manganese dioxide, preferably in solution in petroleum ether, ligroin, benzene, toluene, xylene, cyclohexane, n-hexane, ether, dioxane, chloroform, acetone, methanol, carbon tetrachloride or triethylamine, at a temperature between 20 DEG C. and 140 DEG C. in an atmosphere not containing oxygen, to give b -ionylidene acetaldehyde. In examples (1) b -ionone is condensed with cyanoacetic acid, the reaction being carried out in the presence of tocopherol as an anti-oxidant, whereby partial decarboxylation takes place to give as products b -ionylidene acetonitrile and b -ionylidene cyanoacetic acid, the latter being subsequently converted to b -ionylidene acetonitrile by decarboxylation, the nitrile is hydrolysed to give b -ionylidene acetic acid and reduction of this with lithium aluminium hydride gives b -ionylidene ethanol and (2)-(6) b -ionylidene ethanol prepared as in (1) is oxidized by manganese dioxide to b -ionylidene acetaldehyde. Specifications 633,711 and 668,604 are referred to.
GB9243/52A 1951-04-16 1952-04-10 Improvements in methods of manufacturing -a-ionylidene ethanol and -a-ionylidene acetaldehyde Expired GB745045A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL745045X 1951-04-16

Publications (1)

Publication Number Publication Date
GB745045A true GB745045A (en) 1956-02-22

Family

ID=19822800

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9243/52A Expired GB745045A (en) 1951-04-16 1952-04-10 Improvements in methods of manufacturing -a-ionylidene ethanol and -a-ionylidene acetaldehyde

Country Status (1)

Country Link
GB (1) GB745045A (en)

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