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(R)-(-)-3-氯-1,2-丙二醇合成(R)-(-)-3-氯-2-羟丙基对甲苯磺酸酯的研究(PDF)

《南京林业大学学报(自然科学版)》[ISSN:1000-2006/CN:32-1161/S]

Issue:
2007年06期
Page:
34-38
Column:
研究论文
publishdate:
2007-06-20

Article Info:/Info

Title:
Synthesis of Medicinal Intermediate (R)-(-)-3-chloro-2-hydroxypropyl Tosylate from (R)-(-)-3-chloro-1,2-propanediol
Article ID:
1000-2006(2007)06-0034-05
Author(s):
WANG Shi-fa ZHANG Ming-guang LI Yan-ping
College of Chemical Engineering Nanjing Forestry University, Nanjing 210037, China
Keywords:
(R)-(-)-3-chloro-12-propanediol p-toluenesulfonyl chloride (R)-(-)-3-chloro-2-hydroxypropyl tosylate
Classification number :
TQ227
DOI:
10.3969/j.jssn.1000-2006.2007.06.008
Document Code:
A
Abstract:
Synthesis of the medicinal intermediate (R)-(-)-3-chloro-2-hydroxypropyl tosylate was carried out by the reaction of (R)-(-)-3-chloro-1,2-propanediol and p-toluenesulfonyl chloride in this paper. The influences of the reaction temperature, reaction time, type and dosage of solvent, type and dosage of catalyst, and (R)-(-)-3-chloro-1,2-propanediol/p-toluenesulfonyl chloride ratio on the selectivity of esterification and yield of product were investigated. The suitable synthesis conditions were obtained by optimization with orthogonal experiments: reaction temperature 0°C, reaction time 6h, the molar ratio of p-toluenesulfonyl chloride to (R)-(-)-3-chloro-1,2-propanediol 1.2:1, the molar ratio of catalyst NaOH to (R)-(-)-3-chloro-1,2-propanediol 1.2:1. Ethyl acetate was used as solvent, and the concentration of (R)-(-)-3-chloro-1,2-propanediol was 125g/L. The yield of (R)-(-)-3-chloro-2-hydroxypropyl tosylate was over 85%.

References

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Last Update: 2013-05-20