Hydrochloric Acid → Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Participants

Reaction Steps

4-amino-3-hydroxybenzoic acid (5.0 g, 32.6 mmol) was added dropwise to a 0° C. solution of an HCl 1.25 M solution in MeOH (100 mL) and MeOH (100 mL). After 5 min of final addition the mixture was allowed to warm up to room temperature and stirred overnight. HPLC monitoring of the reaction showed remaining starting material and the mixture was stirred at ambient temperature for 48 hours. The solvent was then removed under reduced pressure and the residue was treated with saturated aqueous bicarbonate solution and the aqueous phase was extracted with AcOEt (2 x). The combined organic extracts were washed with brine, dried over anhydrous sodium sulphate, filtered and concentrated to dryness obtaining the title compound (5.37 g, 97% yield) as a crystalline solid.

Provenance & Evidence