Benzaldehyde → Diethyl (phenylmethylene)malonate

Participants

Reaction Steps

A mixture containing 3.0 mL (19.8 mmoles) of diethyl malonate, 2.0 mL (19.6 mmoles) of benzaldehyde, 0.10 mL of piperidine, and 65 mg of benzoic acid in 35 mL of benzene was heated at reflux for 6 hours with continuous azeotropic removal of water by means of a Dean-Stark trap. Isolation of the product in the manner described in the procedure of Example I, followed by fractional distillation, afforded 4.27 g (88% yield) of diester 8: bp 105°-140° C. (bath temperature, 0.10 mm). Subsequent treatment of diester 8 with 2-nitropropane and sodium ethoxide in ethanol at reflux, as described for the corresponding cyanoester 1 in Example VIII, failed to yield a cyclopropanoid product.

Provenance & Evidence