Studies On The Synthesis Process Of Cyclopentadecanolide

Cyclopentadecanolide as one kind of the macrocyclic musk, which have strong and comfortable musk fragrances, is broadly used in many fields, such as perfume, cosmetic, food, medicines and etc.The process using dodecanedioic acid as starting material to synthesize cyclopentadecanolide(1) is studied in this paper. Dimethyl dodecanedioate(3) was synthesized through the esterfication of dodecanedioic acid(2). The yield was 97%. 12-Oxo-12-(2-oxo-tetrahydrofuran-3-yl)dodecanoate(4) and 12-oxo-12-(2-oxo-tetra -hydrofuran-3-yl)dodecanoic acid(8) were obtained through the Claisen condensation ofγ-butyrolactone and 3 with NaOCH3 as reagent. The sum yield was 69%. 15-Hydroxy-12-oxopentadecanoic acid(5) was prepared from the decarbonation of 4(8) in the presence of alkali metal hydroxide. The yield of 5 was 95%. 15-Hydroxypentadecanoic acid(7) was synthesized through the Huang-Minglong deoxidization of 5 using hydrazine and KOH as reagent. The yield of 7 was 20%. Ultimately, cyclopentadecanolide(1) was derived from 7 through intramolecular cyclization in high temperature and vacuum, with K2CO3 as reagent. The yield was 20%. All the products were confirmed by IR and 1H-NMR spectra. The optimal reaction conditions of each step were determined by feeding method, reactant amount experiment and other condition experiement.The synthesis method use low-priced material, cheap reagent, recycling reactant, and simple process.