绿色氧化法制备联苯类化合物的研究性实验设计与实践

Design and Practice of a Research-Based Laboratory Course on the Synthesis of Biphenyl Derivatives Through Green Oxidation

以苯甲醛和丙酮为原料,利用Robinson增环反应先制备3-甲基-5-苯基环己-2-烯-1-酮,再引导学生设计并研究了水相绿色氧化3-甲基-5-苯基环己-2-烯-1-酮合成联苯类化合物3-乙氧基-5-甲基-1,1′-联苯的影响因素,利用核磁共振确定了产物结构。该研究性实验教学以绿色化学为中心,结合了2步连续反应,产物易提纯且产率高,并开展了开放式大型分析仪器教学和测试,对学生有机合成实验能力和科学研究能力的培养具有很好的教学效果。

Firstly,3-methyl-5-phenylcyclohex-2-ene-1-one was prepared by Robinson cyclization reaction from benzaldehyde and acetone.Then,students were guided to design and study the synthesis of biphenyl derivative of 3-ethoxy-5-methyl-1,1′-biphenyl through green oxidation of it in aqueous phase.The final product was characterized by NMR.Green chemistry is highlighted in this research-based laboratory course.Two-step continuous reaction and the product easy to purify with high yield combined with the open instrumental analysis make it an ideal research-based experiment for the cultivation of students’laboratory skills and scientific research ability in organic chemistry.