对叔丁基杯[6]芳烃六癸酸甲酯醚的合成

以对叔丁基苯酚、甲醛溶液为原料合成了对叔丁基杯6]芳烃;以10-溴代癸酸、甲醇为原料合成了10-溴代癸酸甲酯;对叔丁基杯6]芳烃和10-溴代癸酸甲酯经Williamson醚化反应,合成出对叔丁基杯6]芳烃六癸酸甲酯醚。在n(甲醇)∶n(10-溴代癸酸)=10∶1、催化剂对甲苯磺酸用量为10-溴代癸酸质量的0.6%、反应温度65℃、反应时间3h时,10-溴代癸酸甲酯的收率为67.0%以上。筛选出以氢化钠为Williamson醚化反应的催化剂,在n(对叔丁基杯6]芳烃)∶n(10-溴代癸酸甲酯)∶n(氢化钠)=1∶6∶30、反应时间5h、反应温度70℃时,对叔丁基杯6]芳烃六癸酸甲酯醚的收率为83.3%。用傅里叶变换红外光谱表征了中间体和最终产物的结构,证明了所得化合物的结构与所设计的分子结构相同。

Synthesis of Calix[6] arene Hexa-Decanoic Methyl Ether

p-tert-Butyl calix 6] arene hexa-decanoic methyl ether was prepared from the p-tert-butyl calix 6] arene and 10-bromodecanoic-acid methyl ester. The former was synthesized from p-tert-butylphenol and formaldehyde,and the latter from 10-bromodecanoic-acid and methanol. When mole ratio of methanol to 10-bromodecanoic-acid 10 ∶1,p-toluenesulfonic acid as catalyst,its dosage 0.6%(mass ratio to 10-bromodecanoic-acid),reaction temperature 65 ℃ and reaction time 3 h,yield of 10-bromodecanoic-acid methyl ester is 66.5%. Using sodium hydride as catalyst of Williamson etherification,under the conditions: n(p-tert-butyl calix 6] arene) ∶n(10-bromodecanoic-acid methyl ester) ∶n(sodium hydride) 1 ∶6 ∶30,reaction temperature 70 ℃,and reaction time 5 h,yield of p-tert-butyl calix6] arene hexa-decanoic methyl ether is 83.3%. The intermediates and products were characterized by FTIR. Structures of the compounds were proved to be same with as the designed.