Research On The Synthesis Of Celestolide

As one kind of indane artificial musk, celestolide has stable and strong fragrance which is similar to musk’s odor. Celestolide is widely used in the cosmetic and daily chemical industry as spices agent and is gradually gaining popularity among perfumers with its huge market potential and the great market prospect.In this paper, a five-step method was used in the synthesis of celestolide, and improve the product yield by investigating reaction conditions. The work start with acetylacetic ester and p-tert-butyl benzyl chloride at 100℃, molar ratio of raw materials is 1.2, molar ratio of catalyst and raw material is 0.6%, KOH mixed with ethanol as solvent. The yield of ethyl-2-(p-tert-Butyl)benzylacetoacetate at the optimal condition was 80.5%. The product was hydrolysed under alkaline conditions at 70℃ for 120min, decarboxylated at 100℃ for 90min after neutralizing. The yield of (4-t-butyl)phenyl-2-butanone at the optimal condition was 97.3%. The ketone group in the product was transformed to the alcohol by Grignard reaction, the yield of 4-(4-t-butyl)phenyl-2-methyl-2-butanol was 80.3%. The ring-closing of the product was treated with 88% sulfuric acid at 20℃ for 90min, the yield of 6-t-butyl-1,1-dimethylindane was 57.4%. The final product was transformed by Friedel-Craft acylation. The molar ration of n(matarial):n(acetyl chloride):n(alchlor)=1:1.5:2.25, at 0℃ for 60 min in phenixin solvent. The yield of celestolide was 63.1%.The materials of the five-step to synthesize celestolide are easily gained and the reaction is under mild condition,the yield of the celestolide is 25.0%. The reaction route is flexible, so it has value to synthesize indane derivative and has prospect to musk industry.