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

Abstract

2-hydroxy-N-methyl-N-phenyl-acetamide was synthesized by using N-methylaniline, chloracetyl chloride, anhydrous sodium acetate and methanol through the acetylation, esterfiation 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-phenyl-acetamide(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.

Keywords

-N-methyl-N-phenyl-acetamide / synthesis / acetylation / esterfication / ester interchange / characterization