Methanol → Methyl 3-Hydroxyphenylacetate

Participants

Reaction Steps

To a solution of 3-hydroxyphenyl acetic acid, (5.0 g, 0.033 mol) in methanol (100 mL) was added concentrated sulfuric acid (1 mL) and the reaction mixture stirred at room temperature for 12 hours. After concentration to remove methanol, the crude oil was dissolved in ethyl acetate (75 mL), washed with water (50 ml), saturated aqueous NaHCO3 (50 mL), and brine (50 ml). The organic layer was dried over Na2SO4, and concentrated to give the methyl ester (1) as an oil (5.28 g) in 96% yield, which was used without further purification. 1H NMR (CDCl3) δ 7.17 (t, 1H), 6.81 (m, 3H), 6.48 (s, 1H), 3.69 (s, 3H), 3.57 (s, 2H). 13C NMR (CDCl3) δ 169.9, 153.3, 132.3, 126.9, 118.4, 111.5, 57.8, 38.4.

Provenance & Evidence