Benzene Oxygen Bacterium Ester Synthesis

Kresoxim-methyl was first prepared by BASF which was the first product enterthe market. It is a new class of fungicides chich derived from Strobilurins. Thisfungicide has many advantages broad-spectrum, highly efficient, long duration ofaction and environmentally friendly. These factors make it play a great role infungicide.We have designed a new synthetic route. Kresoxim-methyl was synthesized bycyanide, oximation, methylation, esterification, bromination, etherification reactionand inversion of configuration. o-methyl-benzyl chloride was used as raw material.2-methyl-benzyl cyanide was synthesized from o-methyl-benzyl chloride and sodiumcyanide with tetra-butyl ammonium bromide as phase transfer catalyst.Hydroxy-imino-o-tolyl-acetonitrile was synthesized by the reaction of ethyl nitrite and2-methyl-benzyl cyanide which used sodium ethylate as catalystɑ-methoximino-2-(2-methyl-phenyl)-acetonitrile was synthesized by reaction ofhydroxy-imino-o-tolyl-acetonitrile, dimethyl sulfate and potassium hydroxide.ɑ-methoximino-2-(2-methyl-phenyl)-acetonitrile was also synthesized by means of"one pot process" with ethyl nitrite and2-methyl-benzyl cyanide which used sodiumethylate as catalyst. Then ɑ-methoximino-2-(2-methyl-phenyl)-acetonitrile wasesterified by acid and methanol to give. methyl-2-(2-tolyl)-2-methoxyiminoacetate.the oxime ester was brominated by NBS and then etherified with o-cresol to givemethyl-2-methoxyimino-(2-(o-tolyoxymethyl)phenyl)acetate (E/Z mixture). Afterinversion of configuration with hydrogen chloride as catalyst. We getmethyl(E)-2-methoxyimino-(2-(o-tolyoxy-methyl)phenyl)acetate (Kresoxim-methyl),purity is96.80. The preparation method has high yield, simple operation, mildreaction conditions, low cost and the raw materials easy to get. This method has animportant value of application development.The best synthetic conditions were obtained through a series of experiments onthe catalyst quantity, ratio of input materials, reaction temperature and the reactiontime. The intermediate and final products were characterized by1HNMR, IR, MS.E/Z mixture proportion was tested by high performance liquid chromatography.