Benzoic Acid → Diethyl 2-((5-(4-chlorophenyl)furan-2-yl)methylene)malonate

Participants

Reaction Steps

Diethyl malonate (88 g, 0.55 mole) and 5-(p-chlorophenyl)-2-furaldehyde (104 g, 0.50 mole) were placed in 1.0 liter of benzene containing benzoic acid (10 g) and piperidine (18 ml). The 2.0 liter flask was equipped with a Dean-Stark trap for water removal, and the mixture was refluxed for 4 hours on a steam bath. The mixture was concentrated to an oil under reduced pressure. Washing the residue with benzene (500 ml) yielded a dark solid which was recrystallized from cyclohexane yielding yellow product (111 g, 64% yeild), m.p. 78°-80°.

Provenance & Evidence