Acetic Acid → Ethyl 2-cyano-3-phenyl-2-butenoate

Participants

Reaction Steps

A mixture of p-fluoroacetophenone (100 g, 0.72 mole), ethyl cyanoacetate (81.8 g, 0.72 mole), ammonium acetate (13 g, 0.17 mole) and acetic acid (34.7 g, 0.57 mole) is refluxed for 24 hours in benzene (200 mL) with a continuous removal of water by a Dean Stark trap. The cooled mixture is diluted with benzene (150 mL) and extracted with water (2×300 mL). The organic phase is separated, dried (Na2SO4), filtered and concentrated in vacuo to a brown oil. Kugelrohr distillation (125°-127°/0.03 Torr.) affords 108.4 g (64.3%) of product as a yellow green oil.

Provenance & Evidence