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

doi:10.6023/cjoc201411006

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

ARTICLE

含联苯醚结构2(5H)-呋喃酮衍生物的合成

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

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 E-mail:ltguan@scau.edu.cn;wangzy@scnu.edu.cn
基金资助:
国家自然科学基金(No.31200439)、广东省高等学校人才引进专项资金(No.粤财教[2011]431号)、广东省自然科学基金(No.2014A030313429)资助项目.

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

Guan Litao^a, Mo Guangzhen^b,a, Wu Yancheng^b, Liang Xinyu^b, Luo Qiaofang^b, Wang Zhaoyang^b

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).

1. Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit.PDF(2294KB)

Abstract

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 S_N2 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, S_N2 reaction mechanism

Cite this article

Guan Litao, Mo Guangzhen, Wu Yancheng, Liang Xinyu, Luo Qiaofang, Wang Zhaoyang. Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit[J]. Chin. J. Org. Chem., 2015, 35(5): 1081-1089.

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含联苯醚结构2(5H)-呋喃酮衍生物的合成

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

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