Two-Step Synthesis of 2-(9-Hydroxynonyl)-5,6-dimethoxy-3-methyl-1,4-benzoquinone

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 alkylation

• References

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