Water → 3-(Benzyloxy)-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

To a suspension of 136.8 g (0.60 mol) 3-benzyloxybenzoic acid in 1200 ml dichloromethane 60.6 g (0.6 mol) triethylamine was added at 10° C. A solution of 64.8 g (0.60 mol) ethyl chloroformiate in 100 ml dichloromethane was added over a period of 15 minutes keeping the temperature between 10° C. and 15° C. After stirring for 40 minutes and addition of 58.2 g (0.60 mol) N,O-dimethylhydroxylamine hydrochloride a solution of 60.6 g (0.60 mol) triethylamine was added over a period of 20 minutes at 10–15° C. After additional strirring for 30 minutes water was added and the organic layer dried over sodium sulphate. Fractionated distillation in vacuo yielded 131.9 g (81%) B1.

Provenance & Evidence