毕业设计（论文）《嘧菌酯中间体2-（2-羟基苯基）-3-丙氧基丙烯酸丙酯的合成》.doc

PAGE 邯郸学院本科毕业论文 题 目 嘧菌酯中间体2-（2-羟基苯基）-3-丙氧基丙烯 酸丙酯的合成 学 生 指导教师 讲师 年 级 2009级 专 业 化 学 系 部 化学系 邯郸学院化学系 2013年6月 摘 要 嘧菌酯是一种甲氧基丙烯酸酯类杀虫剂，由于其天然获取量极少，因此人工合成显得很重要，所以嘧菌酯中间体的合成研究引起了研究人员的高度重视。而且由于其专利刚刚过期，国内开始了大量研究，其合成路线已经较为成熟，所以合成工艺优化尤为重要。本文以苯并呋喃酮、丙醇等为原料，通过加成、开环、高温消去等反应，得到嘧菌酯中间体的类似物。并用红外光谱法检验所得产物是否符合预期。第一步选用乙酸酐为催化剂，且苯并呋喃酮，原甲酸三甲酯和乙酸酐1：2：4的摩尔比为最佳。最好的条件是8h，120℃，产率为70%。第二步强碱开环，选用丙醇钠在冰水浴中进行1h；最后先在高温高压条件下干燥1h，然后用KHSO4催化脱甲醇在真空干燥箱中反应三小时。最终通过三步反应得到了嘧菌酯中间体类似物2-（2-羟基苯基）-3-丙氧基丙烯酸丙酯。 关键词 嘧菌酯中间体 杀虫剂 嘧菌酯 红外光谱法 Synthesis of Azoxystrobin intermediate 2 - (2 - hydroxyphenyl) -3 - propoxy propyl acrylate Zhao yanling Directed by Lecturer. Liu shuming Abstract：Azoxystrobin is a strobilurin pesticide. The natural access is limited. So the synthesis of this natural compound is obviously important. The research of azoxystrobin intermediates highly attracted scientists attention. The patent expired recently, and the synthetic route has been relatively fixed after a large number of studies. Thus the synthetic process optimization of this compound is important. In this paper we use phthalide and propanol as raw materials to prepare azoxystrobin intermediate analogue after the process of addition, open-loop and high heat elimination reactions. Also infrared spectroscopy was used to examine the structure of product. In step one, by using acetic anhydride as the catalyst, the phthalide, trimethyl orthoformate and acetic anhydride were reacted with the molar ratio of 1:2:4. The best conditions are 8 hours, 120 centigrade, with yield of 70 percent. In step two, sodium propanol was freshly prepared for opening reaction, and the mixture were stir in ice water bath for 1 hour. Finally, after dried under condition of high temperature and pressure for an hour, the last step was treat the product with KHSO4 in vacuum for 3 hours. By the end of the three-step reaction, intermediate analogue azoxystrobin 2 - (