香豆素-3-羧酸及其酯的合成研究  

Studies on synthesis of coumarin-3-carboxylic acid and its ester

作　　者：刘秀娟[1] 厉连斌[1] 王歌云[1] 

机构地区：[1]江西教育学院理学分院,江西南昌330029

出　　处：《化学试剂》2007年第1期43-45,共3页Chemical Reagents

基　　金：江西省教育厅资助项目[赣财教(2004)18号]

摘　　要：在无水乙醇中,以六氢吡啶为催化剂,通过水杨醛与丙二酸二乙酯的Knoevenagel缩合反应合成了香豆素-3-羧酸乙酯,再经水解、酸化得到香豆素-3-羧酸。对影响香豆素-3-羧酸乙酯收率的原料配比、反应时间、催化剂的选择和用量进行了研究。所得最佳合成条件为:水杨醛与丙二酸二乙酯物质的量比1.0∶1.4,1 mol六氢吡啶用量0.8 mL,反应时间2 h,在最佳工艺条件下,香豆素-3-羧酸乙酯的收率87.6%,质量分数为99.6%。通过IR光谱对产品进行了表征。Ethyl coumarin-3-carboxylate was synthesized from salicylaldehyde and diethyl malonate in absolute alcohol by Knoevenagel condensation reaction using hexahydropyridine as the catalyst. Hydrolysis of the reaction product with sodium hydroxide gave coumarin-3-carboxylic acid. In addition, the influences of the molar ratio of salicylaldehyde to diethyl malonate, the reaction time, the selection and the quantity of catalyst on the yield of ethyl coumarin-3-carboxylate were investigated. The optimum reaction conditions were： n （ salicylaldehyde ）/n （ diethyl malonate） = 1.0 ： 1.4, amount of hexahydropyridine = 0.8 mL （based on 1 mol of salicylaldehyde） and reaction time = 2 h. Under the optimum conditions, the yield of ethyl coumarin-3-carboxylate was 87.6 % with 99.6 % purity. The products were characterized by IR spectrometry.

关 键 词：香豆素-3-羧酸 香豆素-3-羧酸乙酯 水杨醛 丙二酸二乙酯 

分 类 号：O626.31[理学—有机化学]