Sulfuric Acid → Methyl 4-Bromo-3-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-3-hydroxybenzoic acid (30 mmol) in methanol (100 mL) was added concentrated sulfuric acid (2.6 mL). The solution was heated at reflux for 5 hours, cooled to 0° C., and then brought to pH 7 by adding saturated aqueous sodium carbonate. The solution was evaporated to one-third the original volume. Water was added and the product was extracted into ethyl acetate. The organic extracts were washed with water and brine and dried over anhydrous sodium sulfate. Evaporation gave 6.15 g (89%) of the product as a white solid, m.p. 130-132° C.

Provenance & Evidence