Improvement of Friedel-Crafts Acylation Reaction Experiment Applied for Preparation of p-tert-butylacetophenone
ZHANG Jiao1, ZHANG He1, TANG Lei1, YANG Xue1, LI Xue-Qiang1,2
1. School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China;
2. Ningxia Engineering Research Center for Natural Medicines, Yinchuan 750021, China
Abstract In the experiment teaching of basic organic chemistry, the preparation of acetophenone experiment generally use Friedel-Crafts acylation reaction with some problems such as buying acetic anhydride difficultly, not easy to save aluminum chloride catalyst, and so on. This paper improved the Friedel-Crafts acylation using concentrate sulfuric acid as catalyst, phosphorus pentoxide as dehydrating agent, acetic acid as acylating agent reacting with tert-butylbenzene, with molar ratio of 1:0.75:2:1, to prepare the p-tert-butylacetophenone which confirmed by 1HNMR and 13C NMR.This method not only has the advantages of mild reactive conditions,cheap raw materials and simple operation, but also can test students' understanding of positioning effect and hindrance effect of substitutents on aromatic compounds. In addition, vacuum distillation operation is conducive to develop students' experimental skills, and enrich experiment teaching contents.
ZHANG Jiao, ZHANG He, TANG Lei, YANG Xue, LI Xue-Qiang. Improvement of Friedel-Crafts Acylation Reaction Experiment Applied for Preparation of p-tert-butylacetophenone[J]. Chinese Journal of Chemical Education, 2016, 37(14): 27-29.
