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Synthesis of the Key Intermediate of Coenzyme Q10.
- Source :
- Molecules; May2011, Vol. 16 Issue 5, p4097-4103, 7p, 1 Diagram, 4 Charts
- Publication Year :
- 2011
-
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 <superscript>1</superscript>H-NMR, IR and MS. This alternative process has the potential to be used for large-scale process. [ABSTRACT FROM AUTHOR]
- Subjects :
- CHEMICAL reactions
COENZYMES
ISOPRENE
NUCLEAR magnetic resonance
MASS spectrometry
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 16
- Issue :
- 5
- Database :
- Complementary Index
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- 67792605
- Full Text :
- https://doi.org/10.3390/molecules16054097