Convenient Synthesis of 3,3-Dimethylcyclohexylideneacetaldehyde, a sex attractant of the male Boll Weevil

Abstract

In a previous communication¹ we reported on the synthesis of 3,3-dimethylcyclohexylideneacetaldehyde (5a), an important component of the sex pheromone complex of the male Boll Weevil. A key step in this synthesis involved the simultaneous removal of halogen and a double bond from an intermediate poly unsaturated aldehyde by selective reduction. As a part of our investigations on the Vilsmeier formylation of vinylcyclopropanes and dienes², we have found an easy route to aldehyde 4a, and we now show that this aldehyde can serve as an excellent synthon for the preparation of 3,3-dimethylcyclohexylideneacetaldehyde (5a).