有机化学 ›› 2005, Vol. 25 ›› Issue (06): 660-664. 上一篇    下一篇

研究论文

硼氢化钠还原法合成1-(2,4-二氯苯基)-2-氯-乙醇

王明慧,吴坚平,杨立荣*,陈新志   

  1. (浙江大学材料与化工学院 杭州 310021)
  • 收稿日期:2004-07-01 修回日期:2004-12-06 出版日期:2005-05-30 发布日期:2005-05-30
  • 通讯作者: 杨立荣

Synthesis of 1-(2,4-Dichlorophenyl)-2-chloroethanol by Reduction Method with Sodium Borohydride

WANG Ming-Hui, WU Jian-Ping, YANG Li-Rong*, CHEN Xin-Zhi   

  1. (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027)
  • Received:2004-07-01 Revised:2004-12-06 Online:2005-05-30 Published:2005-05-30
  • Contact: YANG Li-Rong

研究了硼氢化钠还原2,2',4'-三氯苯乙酮制备1-(2,4-二氯苯基)-2-氯-乙醇的两种方法. 考察了温度对反应的影响, 对目标产物和副产物的生成机理进行了探讨. 加入氯化钙、氯化镧等金属氯化物能有效促进反应的专一性, 并对其作用机理进行了探讨. 在非质子溶剂如THF中有阳离子树脂的存在下, 还原反应平稳, 具有高产率和高选择性. 对目标产物进行了结构表征.

关键词: 2,2'4'-三氯苯乙酮, 金属氯化物, 1-(2,4-二氯苯基)-2-氯-乙醇, 硼氢化钠, 还原, 非质子溶剂, 阳离子交换树脂

The method of reduction of 2,2',4'-trichloroacetophenone with sodium borohydride to prepare 1-(2,4-dichlorophenyl)-2-chloroethanol was studied. Temperature effect on the reaction was investigated and the mechanism to form objective product and byproducts was discussed. Calcium chloride and lanthanum chloride etc. efficiently improved the reaction specificity. In the presence of amberlyst-732(H) the reaction was smoothly carried out in aprotic solvent such as THF with high yield and specificity. The structure of the objective product was characterized by IR, 1H NMR and 13C NMR spectra.

Key words: sodium boro-hydride, reduction, metal chloride, aprotic solvent, cation amberlite, 1-(2,4-dichlorophenyl)-2-chloroethanol, 2,2',4'-trichloroacetophenone