Abstract

Prio Santoso¹, Chairil Anwar², Jumina², Dwi Siswanta², Suharso³ and Keisuke Ohto⁴

DOI : http://dx.doi.org/10.13005/ojc/340103

Synthesis of a novel calix[4]resorcinarene-chitosan hybrid using vanillin as raw material has been conducted. The synthesis was carried out in four steps i.e. (1) allylation of vanillin, (2) HCl-catalyzed condensation allyl vanillin with resorcinol, (3) chloromethylation of C-4-allyloxy-3-methoxyphenylcalix[4] resorcinarene with paraformaldehyde and HCl in the presence of ZnCl₂ to yield tetrakis-chloromethyl-C-4-allyloxy-3-methoxyphenylcalix[4]resorcinarene, and (4) reaction of tetrakis-chloromethyl-C-4-allyloxy-3-methoxyphenylcalix[4] resorcinarene with chitosan to yield calixarene-chitosan hybrid. Structure elucidation of products were performed using FT-IR, ¹H-NMR, ¹³C-NMR, GC-MS, XRD, and SEM. The product of calixarene-chitosan hybrid was obtained as dark red solid with m.p. > 300 °C in 78% yield.

Calixarene Modification Synthesis; Chitosan Hybrid; Novel Calix[4]resorsinarenes; Vanillin

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