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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (11): 1948-1953. 上一篇    下一篇

研究论文

选择氧化法合成烷基多环苯酰氧基苯甲酸的研究

郑敏燕*,a; 魏永生a ; 安忠维b   

  1. (a咸阳师范学院化学系 咸阳 712000)
    (b西安近代化学研究所 西安 710065)
  • 收稿日期:2007-12-27 修回日期:2008-05-13 发布日期:2008-11-18
  • 通讯作者: 郑敏燕

Synthesis of Multi-ring (p-Alkyl benzoyloxy)benzoic Acids by Selective Oxidation

ZHENG, Min-Yan*,a; WEI, Yong-Shenga ; AN, Zhong-Weib   

  1. (a Department of Chemistry, Xianyang Normal University, Xianyang 712000 )
    (b Xi′an Modern Chemistry Research Institute, Xi′an 710065)
  • Received:2007-12-27 Revised:2008-05-13 Published:2008-11-18
  • Contact: ZHENG, Min-Yan

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被引次数

1 | 1

提出了一种在无水丙酮体系中, 采用KMnO4选择性氧化芳环上醛基的新方法. 运用此法, 氧化烷基多环苯酰氧基苯甲醛制备相应的苯甲酸. 采用循环伏安法研究了KMnO4在丙酮体系中的氧化活性, 利用红外光谱探讨了氧化反应的机理, 产物结构用IR, MS, 1H NMR及元素分析表征. 结果表明, 在无水丙酮体系中, KMnO4的氧化活性明显降低, 可以在芳环上同时存在烷基和醛基时, 选择性氧化醛基, 选择性达100%. 经正交试验确定反应最佳条件为高锰酸钾用量为原料的2倍, 反应时间4 h, 酸解时间1.5 h, 产率94%. 通过对结构类似化合物的合成, 表明该法具有一定的普遍性.

关键词: 选择氧化, KMnO4, 芳香酸, 液晶

A new method of selectively oxidizing aldehyde in anhydrous acetone system with KMnO4 was described. Using this method multi-ring alkyl benzoyloxy benzoic acids were prepared with the corresponding benzaldehydes as reactants. The oxidation activity of KMnO4 in the acetone system was researched by cyclic voltammetry. The mechanism of the reaction was also investigated by IR spectra. The structures of resulting products were confirmed by elemental analysis, IR, MS and 1H NMR spectra. The results showed that the anhydrous acetone system could lower the oxidation activity of KMnO4 remarkably, so in this system, KMnO4 possesses high selectivity to aldehyde as both aldehyde and alkyl groups all localized in a benzene ring. The selectivity was 100%. The optimum conditions of reaction confirmed by orthogonal test design in-clude reactant molar ratio of KMnO4∶reactant＝2∶1, the reaction time of 4 h and acidifying time of 1.5 h with the yield of 94%. Under the optimum condition, some compounds with similar structure were synthe-sized.

Key words: KMnO4, selective oxidation, aromatic acid, liquid crystal