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Molecules 2011, 16(5), 4097-4103; doi:10.3390/molecules16054097
Article

Synthesis of the Key Intermediate of Coenzyme Q10

1,2,†
,
1,2,†,* , 1,2
,
1,2
,
1,2
 and
1,2,*
1 Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China 2 Engineering Research Center of Forestry Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040, China These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 24 March 2011 / Revised: 9 May 2011 / Accepted: 9 May 2011 / Published: 18 May 2011
(This article belongs to the Section Organic Synthesis)
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Abstract

(2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene (4) is the key intermediate in the synthesis of coenzyme Q10 via a coupling reaction with solanesyl bromide. In this paper, we report a simple and effective synthesis of compound 4, starting with the readily available and inexpensive precursors p-toluenesulfonyl chloride (TsCl) and isoprene to obtain (2E)-1-p-toluenesulfonyl-2-methyl-4-hydroxy-2-butene (3) by addition, esterification and hydrolysis. Application of the Friedel-Crafts alkylation to compound 3, followed by the addition of 2,3,4,5-tetramethoxytoluene (TeMT), assembled the two parts into compound 4. The key parameters of each reaction were optimized at the same time, and the four total operations needed to produced compound 4 had a 27.9% overall yield under the optimized conditions. The structures of the compounds were characterized by 1H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process.
Keywords: p-toluenesulfonyl chloride; isoprene; 2,3,4,5-tetramethoxytoluene; (2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene p-toluenesulfonyl chloride; isoprene; 2,3,4,5-tetramethoxytoluene; (2’E)-1-(3-methyl-4-p-toluenesulfonyl-2-butene)-6-methyl-2,3,4,5-tetramethoxybenzene
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mu, F.-S.; Luo, M.; Fu, Y.-J.; Zhang, X.; Yu, P.; Zu, Y.-G. Synthesis of the Key Intermediate of Coenzyme Q10. Molecules 2011, 16, 4097-4103.

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