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有机化学
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有机化学 ›› 1994, Vol. 14 ›› Issue (1): 80-83. 上一篇    下一篇

研究论文

对苯醌-2,5-二羧酸酯的合成

管晓培;于永忠   

  1. 北京理工大学化工与材料学院
  • 发布日期:1994-02-25

The synthesis of benzoquinone-2,5-dicarboxylates

YU YONGZHONG   

  • Published:1994-02-25

氢醌-2,5-二羧酸酯(2a,b)用活性MnO~2氧化高产率地得到对苯醌-2,5-二羧酸酯(3a,b). 氢醌-2,5-二羧酸乙酯(2b)也能用PhI(O~2CCF~3)~2氧化成相应的对苯醌(3b). 在这个反应中,3b可以被环戊二烯捕获,并进一步与CF~3CO~2H反应. 当用2molPhI(O~2CCF~3)~2时, 得到3,6-二-三氟乙酰氧基氢醌-2,5-二羧酸乙酯(6),而在吡啶存在下, 得到6-吡啶基氢醌-2,5-二羧酸乙酯三氟乙酸盐.

关键词: 氧化, 羧酸酯, 活性二氧化锰, 醌, 加成反应

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

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