Synthesis of Vitamin A, intermediates and conversion thereof to

Details Synthesis of Vitamin A, intermediates and conversion thereof to Synthesis of Vitamin A, intermediates and conversion thereof to

1976-03-01

1978-05-30

Thomas, Jr., James O.

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

Organic compounds

Oxygen containing

C07C 2900

Patent

active

040923665

ABSTRACT:
A synthesis of novel Vitamin A intermediates from betaionone 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: 2452386 (1948-10-01), Milas
patent: 2586305 (1952-02-01), Copenhaun
patent: 2602092 (1952-07-01), Oroshnik
patent: 2842600 (1958-07-01), Oroshnik et al.
patent: 2845462 (1958-07-01), Oroshnik
patent: 2920103 (1960-01-01), Oroshnik
patent: 3006968 (1961-10-01), Pasedach et al.
patent: 3949006 (1976-04-01), Oroshnik

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