Synthesis and Bioassay of 2-Naphthylmethanol, a Synthetic Trail Pheromone of Termites

The one-step sodium borohydridereduction of 2-naphthaldehyde to 2-naphthylmethanol is an excellent vehicle for introducing oxidations and reductions to organic chemistry students as well as AP Chemistry students. The experiment described herein also demonstrates the effectiveness of a synthetic trail pheromone for the eastern subterranean termite, Reticulitermes flavipes. As described in the patent literature, the alcohol product 2-naphthylmethanol increases the utility of poisoned baits used to trap termites. A simple but appealing bioassay is described that illustrates this trail-following behavior. The experiment explores many facets of organic chemistry, including pheromones, the stereochemistry of biological receptors, structure determination, and patent literature.