2,3-Dimethoxybenzoic acid → 2,3-Dihydroxybenzoic Acid

Participants

Reaction Steps

2,3-Dimethoxybenzoic acid (2 g, 10.98 mmol) was dissolved in acetic acid (25 mL). Hydroiodic acid solution (25 mL, 47% in water) was added and the reaction stirred under reflux overnight. The reaction was allowed to cool to room temperature and the solvent removed in vacuo. The yellow solid obtained was dissolved in a minimum amount of water and extracted with EtOAc (4×50 mL). Organic layers were combined, washed with Na2S2O3 (10% solution, 2×50 mL), water (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 1.68 g (99%) 2,3-dihydroxybenzoic acid as a white solid. 1H NMR (CD3OD): 7.34 (d, J =8.0 Hz, 1H), 6.99 (d, J=8.0 Hz, 1H), 6.72 (t, J=8.0 Hz, 1H).

Provenance & Evidence