2-Nitropropane → Methyl 2-(4-formylphenyl)benzoate

Participants

Reaction Steps

2-Nitropropane (7.7 ml) and compound C (20.0 g) were added to a solution of sodium (1.52 ) in ethanol (80 ml) and the solution was heated under reflux for 5 hours. Volatile material was removed by evaporation and the residue was partitioned between ether (300 ml) and water (300 ml). The organic phase was separated, washed with saturated sodium chloride solution and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with a mixture of ethyl acetate and hexane (1:9 v/v gradually changing to 1:1 v/v), to give methyl 4'-formylbiphenyl-2-carboxylate (D) (10.2 g) as a waxy solid; NMR (d6 -DMSO): 3.6(s,3H), 7.45-7.6(m,4H), 7.7(d of t, 1H), 7.85(d of d, 1H), 7.95(d,2H), 10.05(s,1H).

Provenance & Evidence