Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (09): 1629-1632. Previous Articles     Next Articles



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

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