4-Methylbenzaldehyde → Diethyl [(4-methylphenyl)methylidene]propanedioate

Participants

Reaction Steps

A mixture of 19.6 mL (166.4 mmol) of p-tolualdehyde, 23.8 mL (158.8 mmol) of diethyl malonate, 0.5 mL of piperidine and 50 mL of benzene was heated at reflux for 18 h using a Dean-Stark water separator. The mixture was allowed to cool to room temperature, benzene was added and it was washed with water (2×), 1N HCl (2×) and NaHCO3. The aqueous phase was extracted with ethyl acetate, the organic phase was dried and the solvent was removed, to yield 41.2 g of the desired product (yield: 99%).

Provenance & Evidence