Acetone cyanohydrin nitrate, reagent

Acetone cyanohydrin nitrate, reagent for nitrating amines to mtra mines, 43, 83... 

Acetone cyanohydrin nitrate, a reagent prepared from the nitration of acetone cyanohydrin with acetic anhydride-nitric acid, has been used for the alkaline nitration of alkyl-substituted malonate esters. In these reactions sodium hydride is used to form the carbanions of the malonate esters, which on reaction with acetone cyanohydrin nitrate form the corresponding nitromalonates. The use of a 100 % excess of sodium hydride in these reactions causes the nitromalonates to decompose by decarboxylation to the corresponding a-nitroesters. Alkyl-substituted acetoacetic acid esters behave in a similar way and have been used to synthesize a-nitroesters. Yields of a-nitroesters from both methods average 50-55 %. 

Acetone cyanohydrin nitrate, a reagent prepared by treating acetone cyanohydrin with nitric acid-acetic anhydride, has been used for the At-nitration of aliphatic and alicyclic secondary... 

The solid superacidic Nafion-Hhas also been found to catalyze effectively nitration reactions with various reagents.503 The nitrating agents employed were n-butyl nitrate, acetone cyanohydrin nitrate, and fuming nitric acid. In nitric acid nitrations, sulfuric acid can be substituted by Nafion-H and the water formed is azeotropically removed during the reaction (azeotropic nitration).503... 

The product obtained from this distillation usually contains small amounts of acetone cyanohydrin acetate, as evidenced by an ester carbonyl band at 1740 cm.-1 in its infrared spectrum. This material does not interfere with the nitration reactions of the reagent. It may be removed by fractionation through a more efficient column. 

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