Synthesis of Methylene-bridged Cyclic Resorcinol Oligomer

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  • Li Daixin
    Graduate School of Natural Science and Technology, Kanazawa University
  • YAMAGISHI Tada-aki
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University
  • NAKAMOTO Yoshiaki
    Department of Chemistry and Chemical Engineering, Faculty of Engineering, Kanazawa University

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  • メチレン結合型レゾルシノール環状オリゴマーの合成
  • メチレン ケツゴウガタ レゾルシノール カンジョウ オリゴマー ノ ゴウセイ

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A convenient synthesis of methylene-bridged cyclic resorcinol oligomer (calix[4]resorcinarene) was reported. First, calix[4]resorcinarene octamethyl ether was prepared by the HCl-catalyzed condensation of 1, 3-dimethoxybenzene with paraformaldehyde in ethylene glycol monoethyl ether. The methoxy group was easily converted to hydroxy group by treatment with BBr3 in chloroform. In 1H NMR spectra, each proton signal of these compounds is singlet. A novel ionophore based on calix[4]resorcinarene octaester was prepared. The ionophore showed higher affinity for larger alkali cations, K+, Rb+ and Cs+, than for smaller ones, Na+ and Li+. The ionophore based on C-methylated calix[4]resorcinarene, which was synthesized from resorcinol with acetaldehyde, on the contrary, did not bind alkali cations.

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