A facile, practical synthesis of 2-(6-methoxy-2-naphthyl) propenoic acid.

T Hiyama, N Wakasa, T Ueda, T Kusumoto

Index: Hiyama; Wakasa; Ueda; Kusumoto Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 2 p. 640 - 642

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Citation Number: 43

Abstract

A facile and practical method for the synthesis of 2-(6-methoxy-2-naphthyl) propenoic acid, a precursor of anti-inflammatory agent naproxen, is described. The method involves (1) Pd- catalyzed ethynylation of 2-bromo-6-methoxynaphthalene,(2) regioselective addition of HX to the triple bond, and (3) Pd-catalyzed carbonylation of the resulting vinyl halide followed by (4) alkaline hydrolysis.