Synthesis of the Key Intermediate of Coenzyme Q10

Molecules

Fan-Song Mu³  Meng Luo¹  Yu-Jie Fu²  Xuan Zhang³  Ping Yu³ 

[1] ¹Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China ²Engineering Research Center of Forestry Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040;¹Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China ²Engineering Research Center of Forestry Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040, China ^†These authors contributed equally to this work.;¹Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin 150040, China ²Engineering Research Center of Forestry Bio-preparation, Ministry of Education, Northeast Forestry University, Harbin 150040, China

关键词: p-toluenesulfonyl chloride;    isoprene;    2;    3;    4;    5-tetramethoxytoluene;   

DOI  :  10.3390/molecules16054097

来源: mdpi

【 摘 要 】

(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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.