Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2412-2419.DOI: 10.6023/cjoc201505022 Previous Articles     Next Articles



王雅珍a, 朱星星b, 林伟a, 郑纯智a, 张继振a   

  1. a 江苏理工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:2015-05-13 修回日期:2015-06-11 发布日期:2015-07-08
  • 通讯作者: 张继振

A Novel Synthetic Method of 3-Methyleneisobenfuran- 1(3H)-one and Their Derivatives

Wang Yazhena, Zhu Xingxingb, Lin Weia, Zheng Chunzhia, Zhang Jizhena   

  1. a School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou 213001;
    b School of Petrochemical Engineering, Changzhou University, Changzhou 213164
  • Received:2015-05-13 Revised:2015-06-11 Published:2015-07-08

A novel and highly efficient synthesis of 3-methyleneisobenzofuran-1(3H)-one and the corresponding derivatives was reported. The new method was characterized with raw material easy to get, low manufacturing cost, mild reaction conditions and high yields. 2-Methylbenzoic acid and their derivatives were used as starting material, methyl 2-((bromotri- phenylphosphoranyl)methyl)benzoate and their derivatives were synthesized through esterification, free-radical bromination with N-bromobutanimide (NBS) and nucleophilic substitution with triphenylphosphine. After Wittig reaction and hydrolysis of carboxylic esters, 2-vinylbenzoic acid and their derivatives were obtained. Then through cyclization reaction with iodine (NBS), 3-iodo(bromo)methylisobenzofuran-1(3H)-one and their derivatives were obtained, which further react by elimination hydrogen halide with 1,8-diazabicyclo[5.4.0]under-7-ene to afford the target compounds. Eleven intermediates were new compounds.

Key words: 3-methyleneisobenzofuran-1(3H)-one, 3-iodo(bromo)methylisobenzofuran-1(3H)-one, derivatives, quaternary alkylphosphonium salt, Wittig reaction, synthesis