Dimethylformamide → N-(3-formylphenyl)acetamide

Participants

Reaction Steps

A mixture of N-(3-hydroxymethylphenyl)acetamide (165 mg, 1.0 mmol), celite (165 mg), pyridinium chlorochromate (645 mg, 3.0 mmol), N,N-dimethylformamide (1.0 mL) and dichloromethane (25 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (40 mL) and washed with aqueous sodium bicarbonate solution (2×30 mL). The organic layer was concentrated and the product purified by chromatography over silica gel using ethyl acetate/hexanes (1:1) as eluant to give 130 mg (81%) of N-(3-formylphenyl)acetamide as a brown solid. MS [M+H] 164.2, 1H NMR (CDCl3) δ (ppm) 9.96 (s, 1H), 8.22 (b, 1H), 8.03 (s, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.61 (d, J=6.6 Hz, 1H), 7.47 (t, J=7.8 Hz, 1H), 2.22 (s, 1H).

Provenance & Evidence