Hydrochloric Acid → N-[(4-Methoxyphenyl)methylidene]hydroxylamine

Participants

Reaction Steps

To a solution of 4-methoxybenzaldehyde (5.0 g, 36.8 mmol) in methanol (300 mL) was added hydroxylamine hydrochloride (7.6 g, 110.4 mmol) and 2N NaOH (37 mL, 73.6 mmol). The mixture was stirred at room temperature for 6 hours. The mixture was neutralized to pH 4 by using 1N HCl. Excess methanol was removed in vacuo to precipitate out the oxime. The precipitations were filtered and washed with water. The product was dried under vacuum and yield a white solid (4.9 g, 88%): 1H NMR (270 MHz, acetone-d6) δ 8.07 (s, 1H), 7.55 (d, J=8.2 Hz, 2H), 6.95 (d, J=8.2 Hz, 2H), 3.82 (s, 3H).

Provenance & Evidence