Synthesis of Pentane-1,5-dialdehydes

Abstract

A general method for the synthesis of alkylpentane-1,5-dialdehydes is described. The appropriately substituted cyclohexanone is oxidized with lead tetra-acetate in benzene solution, and the resultant 2,6-diacetoxycyclohexanone is reduced (lithium aluminium hydride) to the cyclohexane-1,2,3-triol. Fission of the trio1 with sodium periodate yields the pentane-1,5-dialdehyde.