Synthesis and characterization of 2-hydroxy-N-methyl-N-phenyl-acetamide

2-hydroxy-N-methyl-N-phenyl-acetamide was synthesized by using N-methylaniline, chloracetyl chloride, anhydrous sodium acetate and methanol through the, acetylation, esterfication and ester interchange steps. The acetylation of N-methylaniline with chloracetyl chloride, catalyzed by triethylamide with mole ratio n(C6H5NHCH3) : n(ClCH2C(O)Cl): n(N(C2H5)(3)) = 1 : 1.05 : 1, the yield of 2-chloro-N-methyl-N-phenylacetamide(I) was 93.8 %; Then the esterification of I with anhydrous sodium acetate in the presence of phase transfer catalyst tetrabutyl ammonia bromide gave 97.3 % yield of 2-acetoxyl-N-methyl-N-phenyl-acetamide (II); The ester interchange of with methanol catalyzed by potassium hydroxide gave 2-hydroxy-N-methyl-N-phenyl-acetamide (III) in 96.4 % yield. And the total yield was 88.0 %. IR and MS spectroscopy of products were analyzed and their characteristic peaks were assigned. Combining the results of elemental analysis, the molecular structure of I, II and III was identified.