4-Hydroxy-3-iodobenzoic acid (2IPCOOH) → Methyl 4-hydroxy-3-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-3-iodobenzoic acid (59.6 g, 226 mmol) is combined with 3N HCl/MeOH (276 mL, 678 mmol) and heated to 65° C. for 24 h, then concentrated to dryness. The residue is diluted with water, neutralized to pH 7 with 3N NaOH and the resulting solid collected via filtration. The crude material is adsorbed onto silica gel and chromatographed over 1 kg of silica gel with 50% EtOAc/hexane. Fractions containing product are combined and concentrated to a solid (47.2 g). The material is recrystallized from EtOAc to afford 22.8 g (36%) of methyl 4-hydroxy-3-iodobenzoate as a white solid. HRMS (FAB) calcd for C8H7IO3+H: 278.9520, found 278.9534 (M+H)+.

Provenance & Evidence