N-(1-萘基)-4-烷氧基苯甲亚胺席夫碱的合成与表征

Synthesis and characterization of N-(1-naphthyl)-4-alkoxyphenylmethanimine Schiff bases

以对羟基苯甲醛与卤代烃CnH2n+1X(n=2,4,8,14,16)为原料,通过Williamson反应合成对烷氧基苯甲醛中间体,再与α-萘胺缩合得到5个新的含萘基席夫碱化合物。通过对n=8的席夫碱缩合反应进行L9(34)正交试验,得到缩合反应最佳条件:无水乙醇为溶剂,投料物质的量比为1∶1,温度为65℃,时间为8h。中间体及席夫碱系列化合物的结构用FT-IR、1HNMR进行了表征,并利用DSC考察了柔性链碳原子数对席夫碱相态变化的影响。

Five novel Schiff bases were synthesized via the Williamson reaction and Schiff base condensation：p-hydroxybenzaldehyde and alkyl halide CnH2n＋1X（ n = 2,4,8,14, 16） were used as reagents to give the intermediates, p-hydroxybenzaldehyde, which was then subjected to condensation with α- naphthylamine to form the N-（ 1-naphthyl ）-4-alkoxyphenylmethanimine Schiff bases. The optimal reaction conditions were investigated by orthogonal experiments. The structures of the intermediates and Schiff bases were determined by ^1HNMR and FTIR spectra. The phase behaviors were characterized by DSC.