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

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 ml 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 1 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).

1. waitat room temperature for 2 hours
2. concentrationAt the end of this time, it was concentrated by evaporation under reduced pressure, and 1000 ml of toluene
3. additionwere added to the residue
4. washThe solution was then washed with water
5. customthe solvent was removed by evaporation under reduced pressure
6. distillationDistillation

ORD record

ord-e5c859d91d454089b271647a9b610171

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05476848