Ethanol → Ethyl (4-chlorophenyl)acetate

Participants

Reaction Steps

The (4-chlorophenyl)-acetic acid (20.0 g, 106 mmol) was dissolved in 220 mL of ethanol at ambient temperature. A catalytic amount of sulfuric acid (10 drops) was added to afford a light yellow solution. The reaction was allowed to stir overnight to completion and was concentrated to 30 mL. The concentrate was partitioned between ethyl acetate and half-saturated NaHCO3 solution. The aqueous was extracted with ethyl acetate, and the organics were combined. The organic was washed with water, brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired pure (4-chlorophenyl)-acetic acid ethyl ester as a pale yellow oil (21.0 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 7.29 (d, J=8.4 Hz, 2H), 7.22 (d, J=8.4 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 3.58 (s, 2H), 1.25 (t, J=7.2 Hz, 3H).

Provenance & Evidence