The Synthesis of 2,3-Dimethoxy-5-methyl-p-benzoquinone

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Abstract
2,3-Dimethoxy-5-methylbenzoquinone, the key intermediate of the synthesis of coenzyme Q, was synthesized via two new routes. The methylation of 5-nitrovanillin gave 5-nitroveratraldehyde, which was then catalytically reduced to afford 5-aminohomoveratrol. The oxidation of 5-aminohomoveratrol gave 2,3-dimethoxy-5-methylbenzoquinone. 2,3,4-Trimethoxyphenol was obtained by the decarboxylation of 3,4,5-trimethoxysalicylic acid. This was converted via Mannich reaction to 2,3,4-trimethoxy-6-methylphenol, which was then easily oxidized to 2,3-dimethoxy-5-methylbenzoquinone.