Zhou Ming-fan
2013
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Journal
Modern Agrochemicals
Abstract
Optically pure methyl S-2-chloropropionate was prepared starting from methyl R-2-hydroxy propionate,by using Vilsmeier reagent from thionyl chloride and dimethyl formamide(DMF) as chlorinating reagent,DMF also as solvent and catalyst.The effects of some reaction conditions on the yield were researched,for instance,the molar ratio of raw materials,solvents,reaction temperature and time.The optimum conditions of nucleophilic chlorination were as follows: the reaction temperature of 50-60℃,time of 5 h and n(R-2-hydroxy propionate)∶n(Vilsmeier reagent)=1∶ 1.15.The yield was improved from 72% to 89%,compared to the traditional methods which used SOCl2 /pyridine/ PCl5 /POCl3 as chlorinating reagents,and the optical purity(e.e%) was 98.2%.The product structure was characterized by FT-IR,1H NMR and GC-MS.