Synthesis Of Cyclopentadecanone

Muscone is an important type of fragrance. Cyclopentadecanone (exaltone) with natural musk fragrance is an important intermediate for muscone , which are widely used in perfume ,cosmetics, foodstuff , medicinal chemicals and so on.In this paper, synthesis of exaltone was investigated. Dimethylpentadecane- dioate was prepared via pentadecanadioic acid(A) and methanol(B). The molar ratio of A to B was 1:21.Then, dimethyl pentadecanedioate with disperse sodium which was soluted in inert solvent xylene, was cyclized andα-hydroxycyclopentadecanone was obtained at violently refluxing temperature. The reaction product which was not separated was used in next reaction .With xylene as solvent, with zinc / hydrochloric acid as reducting agent, finallyα-hydroxycyclopentadecanone was reducted to obtain the target product exaltone. The intermediate productα-hydroxycyclopentadecanone and target product exaltone were isolated by column chromatography. Their structures are confirmed through IR and NMR spectrum. The appropriate reaction condition was determined by experiments in materiel ratio, reaction time, temperature and solvent. The proper cyclization and reduction conditions were determined that proper molar ratio of sodium to dimethyl pentadecanedioate(1:5.2) ,proper temperature of acyloin condensation was 80-90℃and the temperature of reductive reaction was 75℃with xylene. This rout is short and the reaction condition is simple. It has great industrial application potential.