GB813517A - Improvements in or relating to methods of producing vitamin a - Google Patents
Improvements in or relating to methods of producing vitamin aInfo
- 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
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.
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)
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)
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)
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 |
-
0
- NL NL99527D patent/NL99527C/xx active
-
1956
- 1956-09-11 GB GB27754/56A patent/GB813517A/en not_active Expired
- 1956-09-12 FR FR1169570D patent/FR1169570A/en not_active Expired
- 1956-09-12 DE DEN12710A patent/DE1041950B/en active Pending
Cited By (2)
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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