Reduction of Furan and the Preparation of Tetramethylene Derivatives

During the study of the nitrogen heterocyclics, a convenient method of preparing δ-chlorovaleronitrile was desired. The synthesis developed involved the procedure of Gilman and Louisinian for decarboxylation of furoic acid. The furan obtained was reduced in the presence of palladous oxide palladium black giving a 95 per cent yield of tetrahydrofuran which was split with hydrogen chloride yielding 55 per cent of the theoretical tetramethylene chlorohydrin. Treatment of the chlorohydrin with phosphorus tribromide gave a 98 per cent yield of tetramethylene chlorobromide which gave a 52 per cent yield of δ-chlorovalero nitrile when reacted with sodium cyanide. The chemicals required and the operations involved lend themselves to the preparation of appreciable quantities