Hydrochloric Acid → alpha-Difluoromethoxyimino-o-tolylacetonitrile

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Reaction Steps

Chlorodifluoromethane is passed at 20° C. into a suspension of 18.5 g of the potassium salt of α-hydroxyimino-o-tolylacetonitrile, 1.0 g of 18-crown-6 and 185 ml of dioxane. Simultaneously a solution of 15.96 g of sodium hydroxide in 16.1 ml of water is added dropwise thereto. After subsequently stirring for 3 hours, the reaction mixture is poured onto ice-water and acidified with 2N hydrochloric acid. After extraction with ethyl acetate, the combined organic phases are washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields α-difluoromethoxyimino-o-tolylacetonitrile in the form of a yellow liquid.

Provenance & Evidence