Sodium Chloride → alpha-chloro-N-[2-methylpropoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide

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Reaction Steps

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.9 g; 0.018 mole), 20 ml. of isobutanol and 0.2 ml. of methanesulfonic acid in 150 ml. of xylene was heated at reflux temperature for 2 hours under a soxhlet extractor containing 20 g. of activated 3A molecular sieves. The reaction mixture was then cooled to 26° C. after which time a 2.5% sodium chloride solution was added to the reaction mixture. The layers were separated and the organic layer was dried, filtered and concentrated to yield a yellow solid. The yellow solid was recrystallized from heptane to yield alpha-chloro-N-[2-methylpropoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (5.0 g; 88% yield) as white crystals having a melting point of 107°-110° C. and the following analysis:

Provenance & Evidence