| Coenzyme Q10 is an effective pharmaceutical compound. In this thesis, we have studied on the synthesis of CoenzymeQ10 with the solanesol and 2. 3. 4-trimethoxy-6-methyl-phenolas the mainly starting materials.Firstly, the 2, 3, 4-trimethoxy-6-methyl-phenol is prepared by the bromination of 3. 4. 5-trimethoxybenzocic acid with the aid of cupric ions in an aqueous basic medium. Then the ethoxy carbonyl derivative of salicylic acid was reduced by sodium borohydride to give 0-cresol. And the 6-methyl-2. 3. 4-trimethoxyphenol was obtain in 79. 9%.Secondly, solanesol, 2, 3, 4-trimethoxy-6-methyl-phenyl were used as starting materials, all-E isomer Coenzyme Q10 was synthesized. We have synthesis the Coenzyme in two methods.1. The 2,3,4-trimethoxy-6methyl-phenol and 2-methyl-1, 3-butadiene, solanesol were used as the starting materials. The p-hydroquinone compounds was synthesized from 2,3, 4-trimethoxy-5-methylphenol and chloro-2-methyl-l-phenylsulfonyl-2-butene, then condensed with solanesyl bromide with the sodium ethylate to reduce the sulfone group. Followed by oxidation of the resulting with FeCl3 ยท 6H2O. The overall yield is 27%.2. Monoprotected P-hydroquinone compounds was synthesized from 2, 3, 4-trimethoxy-5-methyl-phenolacetoxyand4-chloro-2-methyl-1-phenyslfonyl-2-butene, then condensed with the solanesyl bromide. The AcO- is reduced at the same time. The following process is the same as the method 1. The overall yield is 44%.The 2,3,4-trimethoxy-6-methyl-phenol was used as the startingmaterial which was oxided smoothly with high yields of the corresponding P-benzoquiones .It is a new method which is better than the methods in which 3, 4, 5-trimethoxytoluene and the 2, 3;4} 5-tetramethoxytoluene was used as the starting material. And an efficient synthetic method for the P-hydroquinone compound containing the C5 transallylic sulfone moiety has been developed by the direct Friedel-Crafts allylation of the protected dihydroquinone with 4-chloro-2-methyl-l-phenylsulfonyl-2-butene. |
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