Ethanol → Diethyl 2,2'-(1,3-phenylene)diacetate

Participants

Reaction Steps

Acetyl chloride (12.5 mL, 175 mmol) was added to a suspension of 2,2′-(1,3-phenylene)diacetic acid (50.0 g, 260 mmol) in ethanol (500 mL) and the resulting solution was heated under reflux for 16 hours. The reaction was then cooled to room temperature and the solvent was removed in vacuo. The residue was partitioned between saturated aqueous sodium hydrogen carbonate solution (300 mL) and ethyl acetate (500 mL). The organic phase was separated and washed with water (200 mL) and brine (300 mL), dried over sodium sulfate and the concentrated in vacuo to afford the title compound as a pale yellow oil in quantitative yield, 63.5 g. 1HNMR (CDCl3, 400 MHz) δ: 1.31 (6H, t), 3.65 (4H, s), 4.20 (4H, q), 7.24-7.36 (4H, m); LRMS ESI m/z 251 [M+H]+

Provenance & Evidence