Hydrochloric Acid → 2-(3,5-Dimethoxyphenylthio)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of thiosalicylic acid (928.1 mg), 5-chloro-1,3-dimethoxybenzene (1.139 g), copper (powder) (222.4 mg), copper(I) iodide (666.6 mg) and N-methyl-2-pyrrolidone (5 ml) was stirred at 200° C. for 5 hours. After cooling, the reaction mixture was adjusted to pH 2 with 4 N hydrochloric acid, extracted with ethyl acetate and washed successively with water and brine. The organic layer was dried over anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (eluting solvent; chloroform:methanol=97:3, 0.1% acetic acid) to give 397.6 mg (23%) of a compound of the indicated formula (10). The compound had a melting point of 182° C.

Provenance & Evidence