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

Synthesis of the Key Intermediate of Coenzyme Q10

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Received: 24 March 2011; in revised form: 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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MDPI and ACS Style

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.

AMA Style

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(5):4097-4103.

Chicago/Turabian Style

Mu, Fan-Song; Luo, Meng; Fu, Yu-Jie; Zhang, Xuan; Yu, Ping; Zu, Yuan-Gang. 2011. "Synthesis of the Key Intermediate of Coenzyme Q10." Molecules 16, no. 5: 4097-4103.


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