Hydrogen Peroxide → Vanillamide

Participants

Reaction Steps

Hydrogen peroxide (3% aqueous solution, 155 mL, 0.151 mol) was added to 4-hydroxy-3-methoxybenzonitrile (5.00 g, 33.52 mmol) at rt. KOH (9.78 g, 148 mmol, 85% purity, reagent grade) was added, resulting in strong gas evolution [exotherm!. The solution stirred at rt for 16 h at which time sodium sulfite (5 equiv.) were added. The reaction mixture was filtered and acidified to pH 2 with HCl (2 N aqueous solution). The aqueous phase was extracted with CH2Cl2 (10×50 mL) until no product was detected by TLC in the organic extract. The combined organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure to give 4.27 g (76%) of the title compound as a pale yellow solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.52 (s, 1H), 7.75 (s, 1H), 7.42 (d, 1H), 7.34 (dd, 1H), 7.10 (s, 1H), 6.76 (d, 1H), 3.78 (s, 3H).

Provenance & Evidence