Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides

Abstract The effects of alkali metal cyanide impregnated on Amberlite XAD resins (KCN/XAD, NaCN/XAD) have been examined using the cyanation of benzoyl chloride. In benzene, benzoyl cyanide was obtained in a very high yield with high selectivity under mild conditions. It is proposed that the reaction occurs on the surface of the resin. On the basis of the result obtained in the absence of any solvent, the reactivity of KCN/XAD toward dimerization of benzoyl cyanide has been found to be much poorer than that of KCN in solution. Although the reaction of acyl chlorides with KCN/XAD or NaCN/XAD in benzene gave various acyl cyanides in good to excellent yields, no aliphatic acyl cyanide could be obtained.