N-[4-(hydroxymethyl)-3-methylphenyl]acetamide → N-(4-Formyl-3-methylphenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

D4 (0.36 g, 2 mmol) and manganese dioxide (0.875 g, 10 mmol) were combined in acetonitrile (16 mL) and heated to 120° C. in the microwave. The solid residue was filtered off and the reaction mixture concentrated. The crude product was purified by column chromatography. Elution with 0-100% EtOAc/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.27 (1H, s), 7.79 (1H, d), 7.50 (1H, d), 7.45 (1H, s), 7.35 (1H, br.s), 2.66 (3H, s), 2.20 (3H, s). MS (ES+): MH+ 178.2.

Provenance & Evidence