Catalystic Additions Of Styrene Oxide And Chiral Separation Of The Adducts

Epoxides are used as starting materials and intermediates in organic synthesis, due to their high reactivity, easy access and being opened under a variety of conditions. Synthesis of 6-substituted by ring opening of epoxides with various nucleophiles was often reported in literatures. According to the principles of green chemistry, the methods and catalysts in the reactions are needed to improve. 2-phenyl-2-alkoxy-ethanol may be used in flavors and medical intermediates, and styrene oxide has been produced in large-scale in China. This paper presented an efficient method of catalytic ring opening of styrene oxide with alcohols. Oxidation of the adducts and chiral separation of the adducts have been studied. The main results were as follows:Five 2-phenyl-2-alkoxy-ethanols were synthesized by additions of styrene oxide and alcohols using sulfuric acid resin as catalyst. The structure of the compounds were determined by IR, MS, NMR .The effects of reaction temperature, reaction time, ratio of reactants and amount of catalyst on the reaction were investigated. Conversion of the reaction can reach over 95%, and its selectivity can get to upwards of 85%. Alcohols are not only reactants but also solvents, which made the separation and purification greatly easier. The stability ,commercially available and cheapness of the catalyst sulfuric acid resin D-72, and ease make up, highly efficient procedure, especially environmentally benign of the reactions, which make this method an excellent and useful green synthetic route. In addition ring opening styrene oxides with water and ammonia were studied.In alkaline conditions, efficient and selective oxidation of 2-phenyl-2-alkoxy-ethanol to the corresponding 2-phenyl-2-alkoxy-...