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

Participants

Reaction Steps

2,2′-(1,3-Phenylene)diacetic acid (10.0 g, 51 mmol) was dissolved in ethanol (100 mL) and the solution treated dropwise with acetyl chloride (2.5 mL). The reaction mixture was stirred at reflux for 18 hours before being allowed to cool and concentrated in vacuo. The residue was taken up in ethyl acetate (100 mL) and extracted with sodium bicarbonate solution (3×50 mL) and brine (3×50 mL). The organic phase was dried (MgSO4), concentrated in vacuo and the residue triturated with pentane to yield the product (11.8 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