2-Chlorophenol → 2-Chlorophenyl propionate

Participants

Reaction Steps

A solution, cooled to 10° C., of 2-chlorophenol (100 g, 0.778 mol) in 250 ml of dichloromethane is slowly admixed with triethylamine (120.7 ml). A solution of 60.7 ml of propionyl chloride in 60 ml of dichloromethane is added slowly dropwise to this mixture over the course of an hour. Following the addition of the propionyl chloride, the mixture is allowed to come slowly to room temperature and is stirred at room temperature for a total of five hours. Following removal of the triethylammonium chloride by filtration, the filtrate is diluted with 100 ml of dichloromethane and washed with 0.1 N hydrochloric acid (500 ml), 0.1 M aqueous sodium hydroxide solution (500 ml) and water (500 ml). The organic phase is dried over sodium sulphate (100 g) for three hours. After the drying agent has been removed by filtration, the solvent is removed on a rotary evaporator. Distillation of the oily yellow residue under reduced pressure gives 129.2 g (90% yield) of 2-chlorophenyl propionate as a colourless liquid (bp 90-93° C./0.3 mm).

Provenance & Evidence