Process for preparation of cinnamate sunscreen agents

Details Process for preparation of cinnamate sunscreen agents Process for preparation of cinnamate sunscreen agents

1994-12-19

1996-06-18

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

562465, C07C 6976

Patent

active

055279473

ABSTRACT:
This invention relates to an improved process for the manufacture of cinnamate compounds, particularly sunscreen agents, useful in cosmetic skin and hair care formulations. The process comprises: (a) dissolving a water insoluble C.sub.1 to C.sub.4 alkoxy benzaldehyde and a C.sub.1 to C.sub.4 alkyl acetate in a common hydrocarbon solvent; (b) reacting the resulting solution in the presence of a strong alkali metal-containing base under mild conditions to form a mixture containing the corresponding C.sub.1 to C.sub.4 alkyl C.sub.1 to C.sub.4 alkoxy cinnamate, the alkali metal salt of the enol corresponding to the C.sub.1 to C.sub.4 alkyl C.sub.1 to C.sub.4 alkoxy cinnamate, the alkali metal salt of a C.sub.1 to C.sub.4 alkoxycinnamic acid, and a C.sub.1 to C.sub.4 alkanol; (c) acidifying the resulting mixture with from about 0.5 to about 1 mole of a strong polybasic acid per mole of base to release acetic acid, to convert the alkali metal salt of the C.sub.1 to C.sub.4 alkoxycinnamic acid to the corresponding C.sub.1 to C.sub.4 alkoxycinnamic acid and to form an alcohol suspension of an alkali metal salt of said strong polybasic acid; (d) esterifying said acetic acid with a C.sub.1 to C.sub.4 alkanol and stripping the resulting acetic acid ester from the mixture; (e) reacting the remaining C.sub.1 to C.sub.4 alkyl C.sub.1 to C.sub.4 alkoxycinnamate and C.sub.1 to C.sub.4 alkoxycinnamic acid with a C.sub.5 to C.sub.14 alkanol in the presence of said strong polybasic acid alkali metal salt suspension at a temperature of from about 60.degree. to about 130.degree. C.; and (f) recovering the C.sub.5 to C.sub.14 alkyl C.sub.1 to C.sub.4 alkoxy cinnamate as a product of the process.

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