1-Butanol → alpha-chloro-N-(butoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.0 g; 0.015 mole), 150 ml. of n-butanol and 0.2 ml. of methylsulfonic acid in 150 ml. of toluene was refluxed for 7 hours in a soxhlet extractor containing 22 g. of activated 3A molecular sieves. The reaction mixture was allowed to cool to 26° C. and was then washed with a 5% sodium carbonate solution. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to yield a dark oil. The dark oil was distilled at 170° C. (0.05 mm) to yield alpha-chloro-N-(butoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (2.7 g; 57% yield) as a clear colorless oil having a boiling point of 170° C. at 0.05 mmHg and the following analysis:

Provenance & Evidence