Water → 1,1-Dimethylethyl N-[4-[(hydroxyimino)methyl]phenyl]carbamate

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Reaction Steps

A solution of (4-formylphenyl)carbamic acid tert-butyl ester (1.0 g), hydroxylamine hydrochloride (0.31 g), and sodium acetate (0.37 g) in ethanol (8.5 mL)/water(1.5 mL) is heated at reflux temperature for 1 hour. The mixture is cooled to ambient temperature and partitioned between diethyl ether and water. The aqueous layer is back-extracted with diethyl ether and the combined organic extracts are washed with saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.8 g pure white solid as the product. MS: m/z 237 (M+H)+.

Provenance & Evidence