4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯的合成研究

摘要：论文的主要目标是研究利用2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙醇进行酯化反应的最佳反应条件，得到产物4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯，最后再对产物进行分离和提纯并进行结构鉴定。用对甲苯磺酰氯与原料2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙醇发生酯化反应，在室温下，先加入2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙醇和吡啶，在冰水浴的条件下，再缓慢加入用吡啶溶解好的对甲苯磺酰氯，缓慢搅拌，反应24h,得到4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯及可能的副产物的混合物产物，并对其进行萃取、干燥、旋转蒸发、点板、纯化等一系列后处理步骤后，得到较纯的最终的目标产物，即4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯。其中，薄层层析的方法对产物进行提纯，梯度洗脱用乙酸乙酯与石油醚的比例为1:4作为展开剂，将原料2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙醇和产物4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯以及可能的副产物等进行分离。实验过程中持续使用点板的方法对当前物料进行比对和确认，收集所需的目标产物并合并。之后再进行相关的图谱分析，对最终产物进行核磁共振氢谱的分析研究，从而确定原料中只有伯羟基发生反应，而叔羟基未参与反应。根据记录下来的相关数据计算得出实验产率达到50%以上。61941

毕业论文关键词：2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙醇;4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯;薄层层析;核磁共振;对甲苯磺酰氯

Research of Synthesis on 4-methyl benzene sulfonic acid-2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-tetra-

hydrofuran-2-yl) ethyl ester

Abstract: This paper mainly aims to study the optimum conditions for ester of 2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethanol ,gaining the product of 4-methyl benzene sulfonic acid-2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-te-

trahydrofuran-2-yl) ethyl ester, and analyze their structures as well as possible by-products. The reduction reaction between 4-methyl benzene sulfonic acid and raw material 2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethanol ，At room temperature, 2-(5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethanol and the part of pyridine were added at first , then the remainder of pyridine and 4-methyl benzene sulfonyl chloride were added at the condition of the ice water bath , the reaction in 24 hours can produce the mixture of 4-methyl benzene sulfonic acid-2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethyl ester and possible by-products. A series of post-processing on the mixture, such as extraction, drying, rotary evaporation, point plate, purification etc., enables to get the final pure target products:4-methyl benzene sulfonic acid-2- (5-(2-hydroxy-propyl-2-

yl)-2-methyltetr-ahydrofuran-2-yl) ethyl ester. The product was purified by thin-layer chromatography.2-(5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethanol, 4-methyl benzene sulfonic acid-2- (5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofu-

ran-2-yl) ethyl ester , and possible by-products were separated by the developing solvent of ethyl acetate and petroleum ether (1:4). During the experiment, materials were compared and confirmed through continuous point plate, thus enabling to collect desired target products and integrating them. Next, the final product was analyzed through H-nuclear magnetic resonance (HNMR),and shown react only primary hydroxyl, however, the tertiary hydroxyl was not involved in the reaction. The experimental yield rate was calculated higher than 50% according to relevant recordings.

Key Words: 2-(5-(2-hydroxy-propyl-2-yl)-2-methyl-tetrahydrofuran-2-yl) ethanol; 4-甲基苯磺酸-2-(5-(2-羟基丙-2-基)-2-甲基四氢呋喃-2-基)乙酯的合成研究:http://www.youerw.com/huaxue/lunwen_67924.html