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Studies On The Synthesis Of Tonalide Musk

Posted on:2009-06-21Degree:MasterType:Thesis
Country:ChinaCandidate:Y B SunFull Text:PDF
GTID:2121360272486616Subject:Organic Chemistry
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Tonalide is an synthetic musk, which has a characteristic flavor and a long lasting scent. It is obtained from the acetylation of the intermediate which chemical name is 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene(HMT), and the key of the synthesis on tonalide is how to synthesize the HMT.It was studied on how to synthesize tonalide and three routes to synthesize the HMT were mainly studied in this paper. One was from p,α-dimethylstyrene and 3,3-dimethyl-butan-2-ol by the catalysis of concentrate sulfuric acid, and the yield effects of HMT such as temperature, stiring speed, material ratio, reaction time were studied. The reaction condition was optimized. Second was from dimethyl-p-tolycarbinal chloride and the mixture of 3,3-dimethyl-1-butene, 2,3-dimethyl-1-butene and 2,3-dimethyl-2-butene by the catalysis of AlCl3, and the mechanisms of reaction of synthesizing HMT from dimethyl-p-tolycarbinal chloride and the three alkenes were discussed. While preparing the HMT from dimethyl-p-tolycarbinal chloride and the mixture of the three alkenes by the catalysis of AlCl3, the yield reached 65%.A new route which was the third route was also studied in this paper. The yield of HMT was up to 70% from dimethyl-p-tolycarbinal chloride and 2,3-dimethyl-2- butene catalyzed by AlCl3.The merit of the new route to synthesize HMT is that the material of the reaction are easily gained and it also has mild condition, good selectivity and high yield, meanwhile, the hydrogen chloride in the reaction can be recycled. So it has a good value both in market and environment, and it also has a wide prospect to the tonalide's industrialization in our country.
Keywords/Search Tags:flavor, tonalide, HMT, balance in alkenes, Fridel-Crafts reaction
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