Sodium Hydroxide → N-[(4-fluorophenyl)methylidene]hydroxylamine

Participants

Reaction Steps

Aqueous sodium hydroxide (70 mL of 50% w/w) was added to a solution of 4-fluorobenzaldehyde (140.5 g, 1.132 mol) and hydroxylamine hydrochloride (86.5 g, 1.25 mol) in ethanol (1 L) and water (2 L), and the reaction was stirred at room temperature for one hour and then adjusted to pH 14 with the addition of 50% w/w aqueous sodium hydroxide. The mixture was extracted with several portions of dichloromethane and then several portions of chloroform. The combined extracts were concentrated under reduced pressure approximately one liter, filtered through a layer of CELITE filter agent and sodium sulfate, and concentrated again under reduced pressure to yield 127 g of 4-fluorobenzaldehyde oxime as a white solid.

Provenance & Evidence