选择氧化法合成烷基多环苯酰氧基苯甲酸的研究  

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

作　　者：郑敏燕[1] 魏永生[1] 安忠维[2] 

机构地区：[1]咸阳师范学院化学系,咸阳712000 [2]西安近代化学研究所,西安710065

出　　处：《有机化学》2008年第11期1948-1953,共6页Chinese Journal of Organic Chemistry

基　　金：陕西省教育厅自然科学基金(No.07JK426);咸阳师范学院科研基金(No.07XSYK219)资助项目

摘　　要：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,1HNMR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4h,酸解时间1.5h,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.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 include 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 synthesized.

关 键 词：选择氧化 KMNO4 芳香酸 液晶 

分 类 号：O625.5[理学—有机化学]