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Synthesis of Gallic Acid Esters and Their Antibloodpatelet Aggregation

Wu Kunxian,Li Minyi,Chen Lin,Chen Xiang (Guangdong Pharmaceutical college,Guangzhou,Postcode 510224)  
p Toluenesulfonic acid was added to facilitate the reactions instead of concentrated sulfuric acid for the synthesis of gallic acid ethyl,propyl,butyl and dodecyl ester,the reaction temperature was risen by a gradient style.Ethyl and propyl gallate were synthesized without water carrying agent.The optimum synthetic conditions were as follow:at a molar ratio of the acid to alcohol to catalyst=0.0825∶0.934∶0.00524 and 120℃ for 4h gave propyl gallate.The overage yield of propyl gallate was 94.2%,ethyl gallate was synthesized in 85.4% yield under the same process as the propyl ester,at a molar ratio of the acid to alcohol to catalyst=0.052∶0.874∶0.00394 gave butyl gallate and 115~128℃ for 5h in 86.8% yield,at a molar ratio of the acid to alcohol to catalyst=0.075∶0.091∶0.012 and 124℃ for 14h with 1,4 dioxane as solvent,4 molecular screen as water absorbing agent gave dodecyl gallate in 93.7% yield,the iso propyl ester was given in the presence of dry hydrogen chloride as catalyst in 88.1% yield under refluxing for 8h at a molar ratio of the acid to alcohol=0.147∶1.37.The dodecyl ester possessed the best action of antibloodpatelet aggregation of the esters.
【Fund】: 广东省科委重点项目
【CateGory Index】: TQ245.24
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