Vitamin A intermediates

Details Vitamin A intermediates Vitamin A intermediates

1975-04-10

1976-03-30

Helfin, Bernard

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260611A, 260617A, C07C 4318

Patent

active

039474984

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: 2452386 (1948-10-01), Milas
patent: 2674621 (1954-04-01), Oroshik
patent: 2845462 (1958-07-01), Oroshnik

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