Synthesis of (Z)- and (E)-4-Oxooct-2-enal

Abstract

The (Z) and (E) isomers of 4-oxooct-2-enal have been prepared from a common starting material, 2-butyl-2,5-dimethoxy-2,5-dihydrofuran, by acid-catalysed ring opening for differing times and acid concentrations. The differences in the mass spectra of the two isomers has allowed positive identification of the (E) isomer as a component of the scent glands of a number of bugs.