Benzene → Ethyl 3-(3,4-dimethoxyanilino)but-2-enoate

Participants

Reaction Steps

4-Aminoveratrole (62.0 g.), ethyl acetoacetate (63.0 g.), benzene (375 ml.), and acetic acid (2.1 ml.) are combined and refluxed in a flask equipped with a Dean-Stark strap to remove water until thin layer chromatography indicated the reaction is complete. The solvent is removed under reduced pressure to give a dark oil which crystallized upon standing. Recrystallization from hexane gives 79.0 g. of a tan powder, m.p. 59°-60° ; a second drop afforded 6.7 g., m.p. 54°-56° . A sample is recrystallized from ethanol/water to give an analytical sample, m.p. 57°-58°.

Provenance & Evidence