The synthesis of benzoquinone-2,5-dicarboxylates

Abstract

Hydroquinone-2,5-dicarboxylates (2a,b) were oxidized by active MnO~2 to benzoquinone -2,5- dicarboxylates (3a,b) in high yield. Diethyl hydroquinone -2,5-dicarboxylate (2b) was also oxidized by PhI(O~2CCF~3)~2 to the corresponding benzoquinone 3b, which could be trapped with cyclopentadiene as well as further reacted with CF~3CO~2H produced in the reaction, When 2mol PhI(O~2CCF~3)~2 was used, diethyl 3,6-bis (trifluoroacetoxy)-hydroquinone-2,5-dicarboxylate (6) was obtained. However, in the presence of pyridine, 6-pyridinio-hydroquinone-2,5-dicarboxylate trifluoroacetate (8) was produced.

Key words: CARBOXYLIC ACID ESTER, QUINONE, OXIDATION, ADDITION REACTION

CLC Number:

O621

Cite this article

YU YONGZHONG. The synthesis of benzoquinone-2,5-dicarboxylates[J]. Chin. J. Org. Chem., 1994, 14(1): 80-83.

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对苯醌-2,5-二羧酸酯的合成