| Questions And Answer(Q&A) | Back Directory | [Preparation]
A 100-ml round-bottomed flask containing 32.4 gm (0.20 mole) of ethyl orthoacetate, 37.2 gm (0.40 mole) of aniline, and 0.10 gm of p-toluenesulfonic acid monohydrate is heated to cause the ethanol to distill rapidly. After a short while, the distillation of ethanol slows down, and the temperature of the flask begins to rise from 90° to 196°C. After 2½ hr, no more ethanol distills, and the reaction mixture is kept overnight at 107°C. The reaction mixture is flash-distilled to afford 13.6 gm of a mixture of aniline and ethyl N-phenylacetimidate. The solid residue is recrystallized from aqueous ethanol to afford 26.4 gm (63%) of colorless crystals, m.p. 134.5-136°C.
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