A Modified Synthesis of 2,15-Hexadecanedione, a Precursor of Muscone, from a Butadiene Telomer

Abstract

Abstract 8-Acetoxy-1,6-octadiene was oxidized with PdCl2/CuCl/O2 to give 8-acetoxy-6-octen-2-one. Hydrolysis and hydrogenation of the ketone produced 8-hydroxy-2-octanone, which was converted to the tosylate after protection of the ketone. The tosylate was converted into the iodide and bromide. The bromide was converted into the Grignard reagent, and coupled with the iodide by the catalysis of CuI coordinated by 2,2′-bipyridyl to give 2,15-hexadecanedione.