Hydrochloric Acid → 1-(3-Methoxy-4-nitrophenyl)ethan-1-one

Participants

Reaction Steps

A suspension of MgCl2 (932 mg, 9.8 mmol) in toluene (13 mL) was treated with triethylamine (4.65 mL, 33.4 mmol), dimethyl malonate (1.9 mL, 16.6 mmol), stirred for 1.5 hours, and treated portionwise over 30 minutes with 3-methoxy-4-nitrobenzoyl chloride (3 g, 13.9 mmol). The reaction mixture was stirred for 45 minutes, then carefully treated with concentrated HCl (4 mL). The layers were separated and the organic phase was dried (Na2SO4), filtered, and concentrated. The, residue was dissolved in DMSO (11.5 mL) and water (0.5 mL), heated to reflux overnight, cooled to room temperature, and partitioned between water and ethyl acetate. The organic phase was washed sequentially with saturated NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 1.63 g (60% yield) of the desired product. MS (ESI(−)) m/e 194 (M−H)−.

Provenance & Evidence