Sodium Hydroxide → 1-Phenyl-2-(3-methoxyphenyl)ethanone oxime

Participants

Reaction Steps

A solution of hydroxylamine hydrochloride (185.5 g, 2.67 mol) water (0.3 L) was added with stirring to a solution of 1-phenyl-2-(3-methoxyphenyl)ethanone (187 g, 0.89 mol) in 95% ethanol (1.4 L). Then, 0.3 L of 20% NaOH was added, with stirring, to the resulting mixture. The mixture was heated to reflux for 2 hrs, cooled, and the alcohol was evaporated with a water aspirator. The aqueous residue was extracted with ether (3×500 ml). The combined ether extracts were dried over MgSO4 and evaporated to provide a solid residue which was then recrystallized from cyclohexane (1 L) to provide 165.5 g (82%) of 1-phenyl-2-(3-methoxyphenyl)ethanone oxime. An analytical sample, recrystallized from ethylacetate/cyclohexane, had mp. 72°-73° C.

Provenance & Evidence