硼氢化钠还原法合成1-(2,4-二氯苯基)-2-氯-乙醇有机化学.pdfVIP

2005 年第 25 卷 有 机 化 学 Vol. 25, 2005 第 6 期, 660～664 Chinese Journal of Organic Chemistry No. 6, 660～664 ·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 (浙江大学材料与化工学院 杭州 310021) 摘要 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 2,24-三氯苯乙酮; 1-(2,4-二氯苯基)-2-氯-乙醇; 硼氢化钠; 还原; 金属氯化物; 非质子溶剂; 阳离子交换树脂 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 (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027) Abstract 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 1 13 objective product was characterized by IR, H NMR and C NMR spectra. Keywords 2,2,4-trichloroacetophenone; 1-(2,4-dichloropheny