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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (9): 1629-1632. 上一篇    下一篇

研究简报

乙酸促进邻甲基苯磺酸铜选择性催化醇和酚的四氢吡喃化反应

王 敏*,a ; 宋志国b ; 姜 恒c ; 宫 红c   

  1. (a渤海大学化学化工学院 锦州 121000)
    (b渤海大学科技实验中心 锦州 121000)
    (c辽宁石油化工大学 抚顺 113001)

  • 收稿日期:2007-12-20 修回日期:2008-03-24 发布日期:2008-09-20
  • 通讯作者: 王 敏

Chemoselective Tetrahydropyranylation of Alcohols and Phenols Catalyzed by Acetic Acid Assisted Copper o-Toluenesulfonate

WANG, Min*,a ; SONG, Zhi-Guob; JIANG, Hengc ; GONG, Hongc   

  1. (a College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121000)
    (b Center for Science & Technology Experiment, Bohai University, Jinzhou 121000)
    (c Liaoning Shihua University, Fushun 113001)
  • Received:2007-12-20 Revised:2008-03-24 Published:2008-09-20
  • Contact: WANG, Min

PDF

1344

被引次数

17

室温无溶剂条件下, 乙酸能有效促进邻甲基苯磺酸铜催化一系列醇或酚和3,4-2H-二氢吡喃反应, 生成相应的四氢吡喃醚. 在乙酸存在条件下, 体系的催化性能有显著提高, 邻甲基苯磺酸铜用量仅需0.3 mol%(占醇或酚的摩尔分数)就能使反应在较短时间内完成. 反应结束后, 邻甲基苯磺酸铜经简单相分离可多次重复使用, 催化活性无明显下降. 产物结构经IR, 1H NMR, 元素分析进行表征.

关键词: 四氢吡喃化, 酚, 乙酸, 醇, 邻甲基苯磺酸铜

Tetrahydropyranyl ethers were synthesized from corresponding alcohols or phenols and 3,4-dihydro-2H-pyran using acetic acid assisted copper o-toluenesulfonate as a synergistic catalyst at room temperature under a solvent-free condition. The catalytic activity of acetic acid assisted copper o-toluenesulfonate was much higher than that without acetic acid under the same conditions. Only the molar ratio 0.3 mol% of copper o-toluenesulfonate to alcohol or phenol was efficient to complete the reaction in a short time. After reaction, the copper o-toluenesulfonate could be recovered easily by simple phase separa-tion and reused many times without distinct loss of its catalytic activity. The structures of products were characterized by IR, 1H NMR spectra and elemental analysis.

Key words: tetrahydropyranylation, copper o-toluenesulfonate, alcohol, phenol, acetic acid