Potassium Carbonate → 4-(3-Thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acid

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Reaction Steps

A mixture of methyl 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoate (12.1 g) and aqueous potassium carbonate solution (50 mL; 10% w/v) in methanol (200 mL) is heated at reflux for 7 hours. It is then concentrated in vacuo and the residue is treated with water (200 mL) and acidified to pH 1 by treatment with hydrochloric acid (1 N), and the resulting solid is quickly filtered off and is then washed with water. The white solid is then azeotroped with cyclohexane in a Dean-Stark apparatus until no more water is removed. The solid is filtered off, to give 4-(3-thienylmethoxy)-2-(2-trimethylsilylethoxy)methoxybenzoic acid (6.03 g), in the form of a white solid.

Provenance & Evidence