4-Toluenesulfonyl chloride → Acetonitrile, 2-(((4-methylphenyl)sulfonyl)oxy)-

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Reaction Steps

Method of preparation: 8.1 g (0.1 mole of glycolonitrile (70% aqueous solution) is added to a cooled (15° -20° C.) mixture of 9.5 g (0.05 mole) of p-toluenesulfonyl chloride in 20 ml. of 1,2-dimethoxyethane and 50 ml. distilled water. A solution of 2.1 g (0.05 mole) of NaOH in 50 ml. distilled water is added slowly with stirring at 20°-25° C. over a period of 6.5 hours, maintaining the pH of the reaction mixture at about 8. The insoluble material is filtered off, washed with cold water, and dried at 40° C. under vacuum to yield 6.8 g (64% conversion) of the product, a light brown solid, m.p. 48°-50.5° C.

Provenance & Evidence