Water → 2-(2-Chloroethoxy)ethyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-chloroethoxy)ethanol (15.3 g, 123 mmol) in toluene (100 ml) kept at 5° C. was added triethylamine (50 g, 500 mmol). A solution of methanesulfonyl chloride (28 g, 245 mmol) in toluene (50 ml) was carefully added keeping the temperature around 5° C. When addition was complete the reaction mixture was stirred at 5° C. for 45 minutes and then 75 minutes at ambient temperature. Water (100 ml) was added and the mixture was stirred for 15 minutes. The phases were separated and the organic phase was washed with water, brine and dried over magnesium sulphate. The solvent was evaporated in vacuo to give crude 2-(2-chloroethoxy)ethyl mesylate as an oil.

Provenance & Evidence