Methanol → Dimethyl (4-methoxy-2-nitrophenyl)methylidenemalonate

Participants

Reaction Steps

A methanol (125 ml) solution of 4-methoxy-2-nitrobenzaldehyde (21.3 g, described in Org. Synth., volume V, p-139, 1973), dimethyl malonate (16.5 g), piperidine (2.5 ml) and acetic acid (0.25 ml) was heated under reflux for 24 hours. The reaction mixture was concentrated, to which was added 1N hydrochloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous potassium carbonate solution and a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2) to obtain the entitled compound (25 g).

Provenance & Evidence