Chloroacetic Acid → 917226-71-2

Participants

Reaction Steps

To a suspension of NaH (9.6 g, 0.4 mol) in DMF (100 mL), a solution of 2-(4-bromophenyl)ethanol (20.1 g, 0.1 mol; see step (i) above) in DMF (100 mL) was added, at 0° C. The resulting mixture was then stirred for 45 minutes at room temperature. After cooling the reaction mixture to 0° C., a solution of chloroacetic acid (9.4 g, 0.1 mol) in DMF (50 mL) was added, and the resulting mixture was stirred at 55 to 60° C. for 3 h. The reaction was quenched by adding cold (about 0° C.) water and then acidification to pH 2.0 (by addition of 1.5 N HCl). The mixture was extracted with ethyl acetate (5×200 mL) and the combined organic layers were washed with water and brine. The sub-title compound was isolated as pale brown solid after evaporation (yield: 14 g, 54%).

Provenance & Evidence