Malonic Acid → HCID 3684868, compound

Participants

Reaction Steps

Malonic acid (7.61 g, 73.1 mmol), 3,4-dichlorobenzaldehye (12.5 g, 71.4 mmol) and ammonium acetate (11.2 g, 146.3 mmol) were heated in ethanol (15 ml) at 55° C. for 15 hours. The solvent was removed under reduced pressure and the resulting white solid was suspended in methanolic hydrochloric acid (2.25M, 100 ml) and heated under reflux for 5 hours. Upon cooling the solvent was removed under reduced pressure and the residue was suspended in water and basified to pH 8 using saturated sodium carbonate solution. The aqueous solution was extracted with dichloromethane (3×) and the combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure. The residual brown oil was purified by column chromatography on silica gel using ethyl acetate as eluant to afford the title compound as a cream solid, 5.72 g.

Provenance & Evidence