1-Propanol → alpha-chloro-N-[propoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide

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Reaction Steps

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.4 g; 0.0161 mole), 150 ml. of n-propanol and 0.2 ml. of methanesulfonic acid was heated at reflux temperature for 9 hours in a soxhlet extractor containing 22 g. of activated 3A molecular sieves. The reaction mixture was allowed to stand at 26° C. for 16 hours and was then concentrated in vacuo yielding a crude product. The crude product was taken up in ether and the ether solution was washed with a 5% sodium carbonate solution. The layers were separated and the organic ether layer was dried over magnesium sulfate, filtered and concentrated in vacuo to yield a white solid. The white solid was recrystallized from hexane to yield alpha-chloro-N-[propoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (3.3 g; 68% yield) as a white solid having a melting point of 83°-85° C. and the following analysis:

Provenance & Evidence