Hydrochloric Acid → 3-(4-Hydroxy-3-methoxybenzoyl)-benzoic acid methyl ester

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Reaction Steps

14.8g of aluminum chloride and 5g of veratrole are added to a solution of 7.34g of isophthalic acid monomethyl ester chloride in 160 ml of dichloromethane under ice cooling. The reaction mixture is refluxed for 8 hours, poured on ice water, acidified with 2 n of hydrochloric acid and shaken out with dichloromethane. The organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel with hexane/ethyl acetate=8/2. 3.5g of 3-(4-hydroxy-3-methoxybenzoyl)-benzoic acid methyl ester of melting point of 133°-134° C. is obtained.

Provenance & Evidence