2-Chloroethanol → Ethyl 2-(2-chloroethoxy)acetate

Participants

Reaction Steps

A suspension of 25.0 g of sodium hydride (as a 60 % w/w suspension in mineral oil) in 100 ml of dimethylformamide was added dropwise to a solution of 50 g of 2-chloroethanol and 104 g of ethyl bromoacetate in 350 m of dimethylformamide at between -45° C. and -40° C., and the mixture was stirred at the same temperature for 1 hour, at between -30° C. and -25° C. for 2 hours, at -5° C. -5° C. for hour and then at room temperature for 2 hours. At the end of this time, it was concentrated by evaporation under reduced pressure, and 1000 ml of toluene were added to the residue. The solution was then washed with water, and the solvent was removed by evaporation under reduced pressure. Distillation gave 77.6 g (yield 75%) of the title compound, boiling at 57°-58° C./2.5 mmHg (333 Pa).

Provenance & Evidence