Sodium Cyanide → Benzeneacetonitrile, 4-(2,2-dimethyl-1-oxopropyl)-

Participants

Reaction Conditions

Reaction Steps

A solution of 34.3 g (0.700 mole) sodium cyanide in 40 ml of water is warmed to 50° C and a solution of α-bromo-p-pivaloyl toluene in 85 ml ethanol is then added dropwise at such a rate as to maintain the temperature at 50° C. After the addition is complete the mixture is refluxed for four hours. The excess ethanol is removed in vacuo and the resulting residue is treated with ether/water. The layers are separated and the ether is washed with cold 50% sulfuric acid, water and sodium bicarbonate, then the ether layer is dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is distilled in vacuo to give p-pivaloyl phenyl acetonitrile (b.p. 143-148° C/0.75 mm n22 =1.5244.)

Provenance & Evidence