Synthesis Of Cyclopentadecanone-an Important Intermediate Product Of Muscone

Muscone is the main component of natural musk and the main source of musk fragrance. (R)-muscone is the main active ingredient of natural musk and plays an important role in the high-grade perfumes, cosmetics and pharmaceutical industries. The synthesis of cyclopentadecanone which is an important intermediate for muscone be of great value in economy. In this thesis, cyclopentadecanone was prepared through condensation reaction and redox reaction regarding pentadecanedioic acid diesters or pentadecane acid bis-lactones based on pentadecanedioic acid as raw material. The main work is as follows:(1) α-hydroxycyclopentadecanone was synthesized through condensation reaction by dimethyl-pentadecanedioate, diethyl-pentadecanedioate or dibutyl-pentadecanedioate repectively both of which were prepared combining pentadecanedioic acid and alcohol. The esterification and cyclization conditions were optimized. The results showed that the α-hydroxycyclopentadecanone prepared by diethylpentadecanedioate obtained a higher yield.(2) Pentadecane acid bis-lactones were synthesized by pentadecanedioic acid and dihydric alcohol (ethylene glycol,1,3-propanediol,1,4-butanediol, diethylene glycol). And conditions of synthesis were optimized.(3) α-hydroxycyclopentadecanone was prepared by pentadecane acid bis-lactones. The results showed that the cyclic ester prepared by pentadecanedioic acid and 1,4-butanediol obtained the highest yield of α-hydroxycyclopentadecanone through condensation reaction.(4) Cyclopentadecanone was synthesized by α-hydroxycyclopentadecanone. And the reducing conditions were optimized.The experimental study indicated that the α-hydroxycyclopentadecanone prepared by pentadecane acid bis-lactones got a higher yield compared to the cyclization process of pentadecanoic dicarboxylic acid diesters and raised a novel method for improving the yield of muscone.