Chloromethyl Methyl Ether → alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

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To a mixture containing alpha-chloro-N-(2,6-dimethoxyphenyl)acetamide (11.0 g; 0.048 mole), 10 ml. of (chloromethyl)methyl ether and 3.0 g. of benzyltriethylammonium bromide in 100 ml. of methylene chloride was added 50 ml. of a 50% sodium hydroxide solution. The temperature of the reaction mixture increased to 40° C. The reaction mixture was stirred for 1 hour after which time the layers were separated, and the organic methylene chloride layer was concentrated in vacuo yielding a white solid. The white solid was recrystallized from isopropanol to yield alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (11.8 g; 90% yield) as a white solid having a melting point of 104°-106° C. and the following analysis:

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