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

Participants

Reaction Conditions

Reaction Steps

N-[4-(Hydroxymethyl)-3-methylphenyl]acetamide (D77) (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 for 7 minutes. The MnO2 was filtered off and the reaction mixture was concentrated to give the crude product which was purified by column chromatography. Elution with 0-100% ethyl acetate/petroleum ether yielded the title compound as a cream solid (0.326 g). δH (CDCl3, 400 MHz) 10.17 (1H, s), 7.77 (1H, d), 7.51 (1H, d), 7.45 (1H, s), 7.36 (1H, br.s), 2.66 (3H, s), 2.22 (3H, s). MS (ES): MH+ 178.2.

Provenance & Evidence