Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1081-1089.DOI: 10.6023/cjoc201411006 Previous Articles     Next Articles



关丽涛a, 莫广珍b,a, 吴彦城b, 梁欣榆b, 罗俏芳b, 汪朝阳b   

  1. a 华南农业大学材料与能源学院 广州 510642;
    b 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006
  • 收稿日期:2014-11-05 修回日期:2014-12-09 发布日期:2014-01-05
  • 通讯作者: 关丽涛, 汪朝阳;
  • 基金资助:


Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit

Guan Litaoa, Mo Guangzhenb,a, Wu Yanchengb, Liang Xinyub, Luo Qiaofangb, Wang Zhaoyangb   

  1. a College of Materials and Energy, South China Agricultural University, Guangzhou 510642;
    b School of Chemistry and Environment, South China Normal University; Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou 510006
  • Received:2014-11-05 Revised:2014-12-09 Published:2014-01-05
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.31200439), the 3rd Talents Special Funds of Guangdong Higher Education (No.Guangdong-Finance-Education [2011]431) and the Natural Science Foundation of Guangdong Province (No.2014A030313429).

Sixteen 5-(4'-alkoxybiphenyl-4-yloxy)-3,4-dihalo-2(5H)-furanones are synthesized via the direct dehydrative etherification reactions of 4'-alkoxybiphenyl-4-ol with mucochloric acid and mucobromic acid, respectively, using sulfuric acid as catalyst at reflux in toluene from 30% to 58% yields (mostly over 47%). The moderate yields may be due to that this acid-catalyzed etherification should be a SN2 nucleophilic substitution reaction. The structures of all newly synthesized compounds are elucidated and confirmed by FTIR, UV, 1H NMR, 13C NMR, and elemental analysis. The synthetic procedures afford not only an important strategy for the synthesis of 2(5H)-furanone derivatives having potential bioactivity, but also a simple method for the synthesis of aromatic ether from two different hydroxyl compounds.

Key words: 2(5H)-furanone, biphenyl structure, synthesis, aromatic ether, dehydrative etherification, SN2 reaction mechanism