(NE)-N-[(2-methylphenyl)methylidene]hydroxylamine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of sodium hydroxide (2.00 g, 50.0 mmol, 1.19 equiv) in water (25 mL) was added to a stirred solution of hydroxylamine hydrochloride (3.30 g, 47.8 mmol, 1.15 equiv) in water (25 mL) at 0° C. The resulting solution was stirred for 10 min at 0° C. Then a solution of 2-methylbenzaldehyde (5.00 g, 41.6 mmol, 1.00 equiv) in ethanol (25 mL) was added slowly over 5.0 min. The resulting solution was allowed to stir for an additional 1 h at RT. The solution was diluted with H2O (100 mL), extracted with ethyl acetate (120 mL) and the organic layers were combined, washed with brine (100 mL), dried over magnesium sulfate and concentrated under vacuum to give (E)-2-methylbenzaldehyde oxime as an off-white crystalline solid. MS m/z 136.0 (M+1). to stir for an additional 1 h at RT extracted with ethyl acetate (120 mL) washed with brine (100 mL) dried over magnesium sulfate concentrated under vacuum