Improved method of production of 9-cis-retinoic acid

Details Improved method of production of 9-cis-retinoic acid Improved method of production of 9-cis-retinoic acid

C - Chemistry, Metallurgy

07

C

C07C 403/20 (2006.01)

Patent

CA 2665909

Improved method of production of 9-(Z)-retinoic acid, in which: a) a .beta.-formyl-crotonic acid C1-C10 alkyl or phenyl ester is reacted with an isolated 9-(Z)-C15-triarylphosphonium salt by the Wittig reaction in the presence of a base to the corresponding 9-(Z)-retinoic acid ester, which b) is then saponified with a base to the corresponding 9-(Z)-retinoic acid carboxylate and then, following protonation with an acid, the desired 9-(Z)-retinoic acid is obtained, and improved method for the enrichment and isolation of the 9-(Z)-C15-triarylphosphonium salt.

Procédé amélioré pour la production d'acide 9-(Z)-rétinoïque, consistant à a) faire réagir un ester alkylique en C1-C10 ou phénylique de l'acide .beta.-formylcrotonique avec un sel de 9-(Z)-C15-triarylphosphonium par la réaction de Wittig en présence d'une base en ester de l'acide 9-(Z)-rétinoïque correspondant et b) saponifier ensuite celui-ci avec une base en carboxylate de l'acide 9-(Z)-rétinoïque correspondant et ensuite, après protonation avec un acide, obtenir l'acide 9-(Z)-rétinoïque souhaité; et procédé amélioré pour l'enrichissement et la séparation du sel de 9-(Z)-C15-triarylphosphonium.

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