Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1881-1888.DOI: 10.6023/cjoc201312011 Previous Articles     Next Articles


郑纯智a, 朱星星b, 赵德建a, 贾洪斌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:2013-12-09 修回日期:2014-03-12 发布日期:2014-05-26
  • 通讯作者: 张继振

Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives

Zheng Chunzhia, Zhu Xingxingb, Zhao Dejiana, Jia Hongbina, 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:2013-12-09 Revised:2014-03-12 Published:2014-05-26

This paper reports a novel and highly efficient synthesis of 3-alkylidene(arylidene)isobenzofuran-1(3H)-one and the corresponding derivatives. The new method is characterized with raw material easy to get, low manufacturing cost, mild reaction conditions and high yields. Isobenzofuran-1(3H)-one (phthalide) and their derivatives were used as starting material. After reacted through free-radical bromination with N-bromobutanimide (NBS), the starting materials were converted to the corresponding 3-bromoisobenzofuran-1(3H)-one and their derivatives, followed by nucleophilic substitution with triphenylphosphine. Then the corresponding Wittig reagents were obtained through elimination reaction by triethylamine, which further react with fatty aldehydes or aromatic aldehydes to afford the target compounds. Thirteen target products and intermediates are new compounds.

Key words: 3-alkylidene(arylidene)isobenzofuran-1(3H)-one, derivatives, quaternary alkylphosphonium salt, Wittig reaction, synthesis