Chloride → 2-(Hydroxyimino)-2-phenylacetonitrile

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Reaction Steps

To 9.07 g (75 mmol) of benzaldoxime in 25 ml of carbon tetrachloride is added dropwise, at 5°, a solution of 45 ml of carbon tetrachloride saturated with 5.6 g (79 mmol) of chlorine gas. The mixture is stirred for 1 hourin an ice bath and then excess chlorine is removed by vacuum. A saturated solution of 7.35 g (150 mmol) of sodium cyanide in water is added dropwise, at 0°, to the thus-prepared phenhydroxamoyl chloride (I; R is phenyl, X is chloro). The mixture is stirred for 2 hours as it is allowed to warm to RT. An excess of aqueous sodium hydroxide is added to dissolve the product into the aqueous solution and then the carbon tetrachloride layer is discarded. The aqueous layer is acidified (HCl) and filtered, and the resulting solid is washed with water and dried to give α-oximinophenylacetonitrile, m.p.=120°-125° (II, R is phenyl).

Provenance & Evidence