Sodium Acetate → Acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester

Participants

Reaction Steps

A solution of acetic acid 4-(2-chloro-acetyl)-3-hydroxy-benzyl ester (2.20 g, 9.07 mmol) and sodium acetate (1.49 g, 18.13 mmol) in anhydrous methanol (40 mL) was heated to reflux for 2 h. The reaction mixture was allowed to cool to RT, and concentrated. The residue was dissolved in dichloromethane and washed with water. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried over Na2SO4, evaporated in vacuo, and the residue was purified by column chromatography (ethylacetate:hexane; 2:8) to give the acetic acid 3-oxo-2,3-dihydro-benzofuran-6-ylmethyl ester as an off white solid (1.29 g, 59%). 1H NMR (CDCl3, 400 MHz) 2.17 (s, 3H), 4.65 (s, 2H), 5.17 (s, 2H), 7.06 (d, J=8.0 Hz, 1H), 7.13 (s, 1H), 7.67 (d, J=8.0 Hz, 1H), 11.67 (s, 1H), 13C NMR (CDCl3, 100 MHz) 20.8, 65.3, 75.1, 112.3, 120.8, 121.2, 124.2, 146.9, 170.5, 174.2, 199.2.

Provenance & Evidence