Synthesis of 2,15-Hexadecanedione, a Precursor of Muscone, From Butadiene

Abstract 1-Acetoxy-2,7-octadiene obtained by the palladium catalyzed dimerization of butadiene in acetic acid was converted to 1-chloro-2,7-octadiene. Coupling of this allylic chloride with iron powder in DMF afforded 1,6,10,15-hexadecatetraene as a main product. Selective oxidation of the terminal double bonds to methyl ketones catalyzed by palladium chloride and cuprous chloride, followed by hydrogenation gave 2,15-hexadecanedione.