A two-step synthesis of 2-methylheptadecane, the sex pheromone of the tiger moth, using the Henry reaction

Abstract

A convenient synthesis of 2-methylheptadecane starting from 1 -nitro-3-methylbutane, via a nitroketone, has been realized in two steps. 2-Methylheptadecane has been isolated and identified as an important component of the sex attractant pheromone of at least nine species of the Artidae family (tiger moth). It has also been characterized as a flavour component in four mango varieties-' and in black soya beans (a variety of Glycine max), as one odorous constituent of the blue-green algae,5commonly called Aoko, and as a chemical component of essential oil6 from Clematis hexapetala Pall and Inula nervosa Wall. Consequently, considerable interest attends a search for its simple synthesis. Although a number of syntheses have been reported, these procedures often exhibit some disadvantages such as low overall yields and/or the need for severe conditions. [excerpt]