Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2344-2349.DOI: 10.6023/cjoc201206030 Previous Articles     Next Articles



张继振a, 吴健b, 王雅珍a, 赵德建a, 贾洪斌a   

  1. a 江苏技术师范学院 化学与环境工程学院 常州 213001;
    b 常州大学石油化工学院 常州 213164
  • 收稿日期:2012-06-30 修回日期:2012-08-30 发布日期:2012-08-31
  • 通讯作者: 张继振

Synthesis of 3-Methyleneisobenzofuran-1(3H)-one and Their Derivatives

Zhang Jizhena, Wu Jianb, Wang Yazhena, Zhao Dejiana, Jia Hongbina   

  1. a School of Chemistry and Environmental Engineering, Jiangsu Teachers University of Technology, Changzhou 213001;
    b School of Petrochemical Engineering, Changzhou University, Changzhou 213164
  • Received:2012-06-30 Revised:2012-08-30 Published:2012-08-31

Starting from 2-vinylbenzoic acid methyl ester and derivatives, 3-hydroxymethylisobenzofuran-1(3H)-one and derivatives were prepared through hydrolysis of esters, followed by epoxidation with m-chloroperoxybenzoic acid, cyclization reaction catalyzed by p-toluenesulfonic acid; then nucleophilic substitution with phosphorus tribromide or tosyl chloride and elimination reaction, 3-methyleneisobenzofuran-1(3H)-one and their derivatives were synthesized. The yield of tosyl chloride method was higher than phosphorus tribromide method in the nucleophilic substitution and elimination reaction. Ten target products and intermediates are new compounds. Their structures were characterized by 1H NMR, 13C NMR, MS and IR techniques. The target products did not dimerize in air over a few weeks.

Key words: 3-methylereisobenzofuran-1(3H)-one, protoanemonin, derivatives, synthesis