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联萘二甲酸的合成与拆分
Synthesis and Optical Resolution of 1,1′-binaphthyl-2,2′-dicarboxylic Acid
【摘要】 光学纯的联萘二甲酸是不对称催化反应的重要催化剂和合成中间体,但由于制备困难,目前并未得到广泛的应用.以廉价的2-甲基萘为原料,经过2次溴代、水解成醇,继而氧化成羧酸,再经酯化、乌尔曼偶联反应、水解得到消旋的联萘二甲酸,然后用奎宁拆分,最终生成光学纯的联萘二甲酸.操作简单安全,原料廉价易得,拆分前总收率为50.8%,最终产品的光学纯度值为99%.
【Abstract】 Optical purity 1,1′-Binaphthyl-2,2′-dicarboxylic Acid(1)are important catalyst of asymmetric catalysis and synthetic intermediates.However,due to difficulties in their preparation,it haven′t a wide range of research and application yet.The cheap 2-methylnaphthalene was used as raw materials,after two bromide,hydrolyze into alcohol,oxidate into acid,esterify,ullmann coupling reaction,hydrolyze into rac-1,then optical resolve by quinine,the resulting chiral-1.The whole route is reasonable designed,simply and safely operated,raw materials cheap and readily available,total yield before optical resolution is 50.8%,the value of ee of the final product is 99%,which has good prospect of industrialization,make a foundation for the future development of this kind of catalyst.
【Key words】 1,1′-binaphthyl-2,2′-dicarboxylic acid; synthesis route; optical resolution; yield;
- 【文献出处】 武汉理工大学学报(交通科学与工程版) ,Journal of Wuhan University of Technology(Transportation Science & Engineering) , 编辑部邮箱 ,2012年04期
- 【分类号】TQ245.13
- 【下载频次】101