Benzaldehyde → alpha-Cyanocinnamic acid ethyl ester

Participants

Reaction Steps

A mixture of benzaldehyde (0.6 mol, 63.7 g), ethyl cyanoacetate (0.6 mol, 67.8 g) and piperidine (1 mL) in EtOH (60 mL) was stirred overnight. The clear solution was then placed in an ice-water bath to initiate the crystallization. The crystalline material was filtered, washed with EtOH and dried in a vacuum oven at 50° C. to give 58.27 g of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester. The mother liquors and the washings were concentrated under reduced pressure; the residue was cooled in an ice-water bath to produce more crystalline product. This material was collected by filtration and washed with hexane, and a mixture EtOH/hexane (1/4), it was then dried in a vacuum oven at 63° C. to give 38.01 g of (E)-2-cyano-3-phenyl-acrylic acid ethyl ester (80% combined yield).

Provenance & Evidence