4-Methoxybenzaldehyde → N-[(4-Methoxyphenyl)methylidene]hydroxylamine

Participants

Reaction Steps

4-Methoxybenzaldehyde (10.0 g, 73.4 mmol) was dissolved in 200 mL of ethanol. A solution of hydroxyamine hydrochloride (6.38 g, 91.8 mmol) in 50 mL of H2O was added followed by a solution of sodium acetate (12.1 g, 146.8 mmol) in 50 mL of H2O. The mixture was stirred at room temperature under N2 for 12 h. The ethanol was removed in vacuo and the aqueous mixture was extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and concentrated to afford 12.8 g of light yellow oil. 1H NMR showed it was 80% pure (92% yield). This material was taken into the next step without further purification. (CDCl3): δ 2.15 (s, 1H); 3.83 (s, 3H); 6.92 (d, 2H); 7.50 (d, 2H); 8.10 (s, 1H).

Provenance & Evidence