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
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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.
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.
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.