Intermediates for Vitamin A

Details Intermediates for Vitamin A Intermediates for Vitamin A

1976-02-17

1978-04-04

Garner, Vivian

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

2604381, 260611A, 260611V, 260612R, 560106, 560105, 260613R, 260617A, C07C17500

Patent

active

040827917

ABSTRACT:
A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.

REFERENCES:
patent: 2819314 (1958-01-01), Aroshnik

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