GB813517A - Improvements in or relating to methods of producing vitamin a - Google Patents

Improvements in or relating to methods of producing vitamin a

Info

Publication number
GB813517A
GB813517A GB27754/56A GB2775456A GB813517A GB 813517 A GB813517 A GB 813517A GB 27754/56 A GB27754/56 A GB 27754/56A GB 2775456 A GB2775456 A GB 2775456A GB 813517 A GB813517 A GB 813517A
Authority
GB
United Kingdom
Prior art keywords
vitamin
aldehyde
ester
ionylidene
acetic acid
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
GB27754/56A
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.)
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 GB813517A publication Critical patent/GB813517A/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
    • 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
    • C07C403/18—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 nitrogen 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

In a process for the preparation of Vitamin A, b -ionone is condensed by the Knoevengeal method, with cyano-acetic acid or an ester thereof, the condensate, after the hydrolysis of any b -ionylidene cyano-acetic acid ester formed, being decarboxylated, the b -ionyl-idene acetonitrile formed being converted by means of a di-alkyl-aluminium hydride into the corresponding aldimine complex which is hydrolysed in an aqueous medium to obtain b -ionylidene acetaldehyde, followed by the condensation of the aldehyde obtained by means of acetone to obtain the "C18-ketone," which ketone is condensed by the Knoevenagel method with cyanoacetic acid or an ester thereof, the condensate, after hydrolysis of any ester formed, being converted by means of a di-alkyl-aluminium hydride into the corresponding aldimine complex which is hydrolysed in an aqueous medium to obtain Vitamin A aldehyde, which aldehyde is reduced to Vitamin A by means of di-alkyl-aluminium hydride, a trialkyl-aluminium compound, a complex metal-hydride containing two different metal atoms or any other reducing agent which reduces the aldehyde group to an alcohol and does not affect the double bonds. Preferably the condensation between the C18 ketone and/or the b -ionone with cyano-acetic acid or ester thereof takes place in the presence of acetamide, ammonium acetate or mixtures thereof with acetic acid, toluene, benzene or mixtures thereof; the reduction of b -ionylidene acetonitrile and/or of Vitamin A acid nitrile or of Vitamin A aldehyde is effected by means of a dialkyl-aluminium hydride or a trialkyl aluminium compound the alkyl groups of which contain 1-6 carbon atoms, under anhydrous conditions, with the exclusion of oxygen, preferably in a nitrogen atmosphere, at a temperature between - 50 DEG and + 50 DEG C., and in the presence of an inert solvent, preferably an aliphatic or aromatic hydrocarbon or an aliphatic or alicyclic ether. The reduction of b -ionylidene acetonitrile or Vitamin A acid nitrile is preferably effected between equimolar quantities of the reactants. An example of the preparation of Vitamin A by the process of the invention is given. The preparation of the semicarbazone of Vitamin A aldehyde is also described. Specifications 801,417 and 811,527 are referred to.
GB27754/56A 1955-09-14 1956-09-11 Improvements in or relating to methods of producing vitamin a Expired GB813517A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL813517X 1955-09-14

Publications (1)

Publication Number Publication Date
GB813517A true GB813517A (en) 1959-05-21

Family

ID=19838789

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27754/56A Expired GB813517A (en) 1955-09-14 1956-09-11 Improvements in or relating to methods of producing vitamin a

Country Status (4)

Country Link
DE (1) DE1041950B (en)
FR (1) FR1169570A (en)
GB (1) GB813517A (en)
NL (1) NL99527C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110950791A (en) * 2019-12-09 2020-04-03 万华化学集团股份有限公司 Vitamin A and preparation method of vitamin A ester

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2623805B1 (en) * 1987-12-01 1990-04-13 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF VITAMIN A

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE857952C (en) * 1950-07-12 1952-12-04 Philips Nv Process for the preparation of ª-ionylideneacetaldehyde
GB717904A (en) * 1949-07-16 1954-11-03 Philips Nv Improvements in or relating to methods of producing ª‰-ionylidene acetaldehyde
DE918987C (en) * 1950-11-25 1954-10-11 Eastman Kodak Co Process for the synthesis of vitamin A active compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110950791A (en) * 2019-12-09 2020-04-03 万华化学集团股份有限公司 Vitamin A and preparation method of vitamin A ester
CN110950791B (en) * 2019-12-09 2021-12-14 万华化学集团股份有限公司 Vitamin A and preparation method of vitamin A ester

Also Published As

Publication number Publication date
FR1169570A (en) 1958-12-31
DE1041950B (en) 1958-10-30
NL99527C (en)

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