THE PREPARATION OF TRIPHENYLMETHANE AND THE ACTION OF HEAT ON THE ETHERS AND ESTERS DERIVED FROM TRIPHENYL CARBINOL
THE PREPARATION OF TRIPHENYLMETHANE AND THE ACTION OF HEAT ON THE ETHERS AND ESTERS DERIVED FROM TRIPHENYL CARBINOL
复制标题
三苯基甲烷的制备以及三苯基甲醇衍生的醚和酯的热作用
DOI：
10.1021/ja01676a033
复制
发表时间：
1924
期刊：
影响因子：
--
通讯作者：
R. C. Young
中科院分区：
文献类型：
--
作者：
J. F. Norris;R. C. Young
关于含氯化铝的某些有机分子化合物的化学性质的研究，化合物1(CeH6)8CCl的行为。研究了AlCl3与多种物质的作用。当等分子量的三苯基氯甲烷和三氯化铝溶解在乙醚中，溶液放置几个小时后，发生反应，生成三苯基甲烷的混合物，产物不分解就不能结晶或蒸馏。对该反应进行了研究，目的是开发一种制备三苯甲烷的改进方法，并阐明其反应机理。2在实验部分给出了以四氯化碳、苯、醚和氯化铝为原料在高纯度条件下制备三苯甲烷的具体方法。该过程不涉及三苯基氯甲烷的分离，并且易于进行。单次结晶后纯碳氢化合物的产率为按氯化铝用量计算的的%。苯甲酰氯和三氯化铝的化合物与乙醚反应生成苯甲酸乙酯。在氯化锌存在下，苯甲酰氯和乙醚生成苯甲酸乙酯和氯化乙酯。三苯基氯甲烷似乎也有可能发生类似的反应。反应的第一步是生成三苯基甲基乙基醚和乙基氯。在这种情况下，三苯基甲烷的最终形成将是首先产生的三苯基甲基乙基醚的分解。为了验证这一观点，将乙醚溶解在含有氯化铝的乙醚中。反应的产物和以前一样是三苯甲烷和一种胶状物质。当三苯基氯甲烷和三氯化铝溶解在正丁基醚中时，发生转化为三苯甲烷。
In connection with the study of the chemical properties of certain organic molecular compounds containing aluminum chloride, an account ofwhich will be published later, the behavior of the compound1 (CeH6) 8CCl. AlCl3 with a number ofsubstances has been investigated. When equal molecular quantities of triphenyl-chloromethane and aluminum chloride are dissolved in ether and the solution is allowed to stand for several hours, a reaction takes place as the result of which there is formed a mixture of triphenyl-methane and a product that could not be crystallized or distilled without decomposition. This reaction has been studied with the object of develop-ing an improved method for the preparation of triphenylmethane and with the view of elucidating its mechanism. 2 Detailed directions are given in the experimental part of the paper for the preparation in a high state of purity of triphenylmethane from carbon tetrachloride, benzene, ether and aluminum chloride. The procedure does not involve the isolation of triphenyl-chloromethane, and can be carried out readily. The yield of pure hydrocarbon after a single crystallization wras 64% of that calculated based on the aluminum chloride used. The compound of benzoyl chloride and aluminum chloride reacts with ether to form ethyl benzoate. In the presence of zinc chloride, benzoyl chloride and ether yield ethyl benzoate and ethyl chloride. It seemed probable that a similar reaction would take place in the case of triphenyl-chloromethane. The first step in the reaction would be the formation of triphenylmethyl ethyl ether and ethyl chloride. In this case the ultimate formation of triphenylmethane would result from the decomposition of the triphenylmethyl ethyl ether first produced. To test this view the ether was dissolved in ethyl ether containing aluminum chloride. The products of the reaction were as before, triphenylmethane and a gummy substance. Whentriphenyl-chloromethane and aluminum chloride were dissolved in normal butyl ether the transformation to triphenylmethane took place.