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Synthesis 2014; 46(17): 2371-2375
DOI: 10.1055/s-0033-1338643
DOI: 10.1055/s-0033-1338643
paper
Two-Step Synthesis of 2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone
Further Information
Publication History
Received: 21 February 2014
Accepted after Revision: 23 April 2014
Publication Date:
28 May 2014 (online)
Abstract
2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone was readily synthesized from commercially available 3,4,5-trimethoxytoluene in two steps. First, 2,3-dimethoxy-5-methyl-1,4-benzoquinone (coenzyme Q0) was obtained in one step by treatment of 3,4,5-trimethoxytoluene with hydrogen peroxide under metal-free conditions, followed by free-radical alkylation with 10-hydroxydecanoic acid in the presence of potassium peroxodisulfate and silver nitrate in a mixed solvent (MeCN–H2O, 1:1) to afford the title compound in good yields (60%, based on coenzyme Q0).
Key words
coenzyme Q0 - decarboxylative cross-coupling - idebenone analogue - free-radical alkylationSupporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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