Methanol → Methyl 3-Hydroxyphenylacetate

Participants

Reaction Steps

3-Hydroxyphenylacetic acid (75.3 g, 0.5 mol) was dissolved in methanol (900 mL). Concentrated sulfuric acid (2 mL) was added and the mixture refluxed for 5 hours. The solvent was evaporated and the residue dissolved in ethyl acetate (1000 mL) and washed with water (2×600 mL) and brine, and dried (MgSO4). Solvent was evaporated to afford methyl 3-hydroxyphenylacetate as an oil (82 g, quantitative yield). 1H NMR (500 MHz, CDCl3) δ 7.2 (1H, t), 6.9-6.75 (3H, m), 5.5 (1H, br), 3.75 (3H, s), 3.63 (2H, s).

Provenance & Evidence