Synthesis of a trimeric lignin model compound composed of a-O-4 and b-O-4 linkages under microwave irradiation

作     者：Xin-Ping Ouyang Chun-Lei Liu Yu-Xia Pang Xue-Qing Qiu 

作者机构：School of Chemistry & Chemical EngineeringSouth China University of Technology 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2013年第24卷第12期

页      面：1091-1094页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070305[理学-高分子化学与物理] 080501[工学-材料物理与化学] 0805[工学-材料科学与工程（可授工学、理学学位）] 0703[理学-化学] 

基　　金：financially supported by the National Basic Research Program of China (No. 2012CB215302) National Natural Science Fundation of China (No. 20876064) the Guangdong Provincial Natural Science Fund (No. 9151064101000082) 

主　　题：Lignin Microwave irradiation Model compound Synthesis 

摘      要：A trimeric lignin model compound composed of α-O-4 and β-O-4 linkages was prepared by the microwave-assisted synthesis, which consisted of three steps： （a） the synthesis of 3-methoxy-4- benzyloxyacetophenone （2） from acetovanillone （1）, （b） the bromination of compound 2 to produce 3- methoxy-4-benzyloxy-α-bromoacetophenone （3）, and （c） followed by a nucleophilic substitution of compound （3） to obtain 3-methoxy-4-benzyloxy-α-（3-methoxy-4-（1-propenyl）phenol）-acetophenone （4）. The target product was characterized by MS, 1H NMR and 13C NMR spectroscopy. It was found that the trimeric compound synthesized can be used as a preferable lignin model compound because it contains guaiacyl structural unit （3-methoxy-4-hydroxy phenyl propane） linked by α-O-4 and β-O-4 linkages. In addition, under the conditions of microwave irradiation, the reaction time of each step is significantly reduced, and the selectivity of target product is greatly improved. The yields of each step and the overall sequence are 95.31%. 87.3%. 90.6% and 75.4% （95.31%× 87.3% × 90.6%）. respectively.