两步法合成四种芳基苄基酮

SYNTHESES OF FOUR ARYL BENZYL KETONES WITH TWO STEPS

以氯化苄和对位取代的苯甲醛为起始原料,首先通过格氏法合成了4个芳基苄基甲醇先行体,进一步经硅胶负载氯铬酸吡啶(PCC)氧化合成了4个相应的芳基苄基酮。目标产物总分离产率均在70%以上。通过IR、1 H NMR、13 C NMR对所有8个合成化合物的分子结构进行了分析表征。分别对格氏反应法制备芳基苄基甲醇和氯铬酸吡啶盐催化氧化法合成芳基苄基酮的反应机理作了初步探讨。以苯基苄基甲醇以及苯基苄基酮的合成为例,讨论了各种因素对反应的影响。

Four aryl benzyl methanol precursors were initially synthesized starting with benzyl chloride and para-substituted benzaldehydes by the Grignard method.Four corresponding aryl benzyl ketone products were further synthesized by oxidation with pyridium chlorochromate loaded on silicon gel.The overall isolate yields for all the target products were above 70%.The molecular structures of all 8 synthesized compounds were characterized by Infrared spectroscopy,^1H NMR and ^13C NMR spectroscopy.Preliminary mechanism was discussed for the synthesis of aryl benzyl methanol by Grignard method and for that of aryl benzyl ketone by catalytic oxidation with pyridium chlorochromate.Effects of various factors on reactions were explored and discussed exemplified by synthesis of phenyl benzyl methanol and phenyl benzyl ketone.Optimal conditions were proposed.