Sodium Cyanide → 2-(Hydroxyimino)-3-methoxy-3-methylbutanenitrile

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Reaction Steps

53.6 g (0.46 mol) of 2-methoxy-2-methylpropionaldehyde oxime in diethyl ether (about 1M) are initially taken at from -5° to 10° C. 35.8 g (0.5 mol) of chlorine gas are passed in, after which stirring is carried out for 1 hour at this temperature, the mixture is evaporated down at 10° C. and the residue is taken up in diethyl ether. 24.7 g (0.5 mol) of sodium cyanide in 375 ml of 20:1 methanol/water are initially taken at 10° C. and the above ether solution is rapidly added dropwise. After 4 hours at room temperature, solid components are removed from the mixture and the solution is washed with 2 times 100 ml of methanol. The combined solutions are evaporated down and the residue is partitioned between methyl tert-butyl ether and water. Drying the organic phase (sodium sulfate) evaporating down and crystallizing (dichloromethane/n-hexane) leads to 41.1 g (63% of theory) of a white powder of melting point 102°-104°-C.

Provenance & Evidence