The preparation of 13-(z)-retinoic acid

Details The preparation of 13-(z)-retinoic acid The preparation of 13-(z)-retinoic acid

C - Chemistry, Metallurgy

07

C

C07C 403/20 (2006.01) C07C 51/353 (2006.01)

Patent

CA 2119513

13-(Z)-Retinoic acid of the formula (I): (See formula I) is prepared by: a) reacting 5-hydroxy-4-methyl-2(5H)-furanone with a [3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4- pentadienyl]triarylphosphonium salt and b) subsequently partially isomerizing the resulting mixture of 13-(Z)- and 11,13-di-(Z)-retinoic acid, where the reaction in step a) is carried out in the presence of lithium hydroxide as alkali metal hydroxide and in dimethylformamide as solvent at from +10 to -9°C and/or the isomerization in step b) is carried out by irradiating the mixture of isomers obtained in a) in an organic solvent in the presence of a photosensitizer with light in the wavelength range from 200 to 600 nm.

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