Synthesis of Cyclopentadecanone by Ring Contraction of Cyclohexadecanone

Article abstract of DOI:10.1246/bcsj.53.823

Cyclopentadecanone has been synthesized from cyclohexadecanone. 2,2,15-Tribromocyclohexadecanone, upon treatment with sodium methoxide, underwant the Favorskii rearrangement via methyl 2-bromo-1-cyclopentadecene-1-carboxylate to produce a mixture of methyl 2-methoxy-1-cyclopentadecene-1-carboxylate, methyl 2-methoxy-2-cyclopentadecene-1-carboxylate, and methyl 2,2-dimethoxycyclopentadecane-1-carboxylate which was converted into cyclopentadecanone.