SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION

• Main Authors: Suryadi Budi Utomo, Jumina Jumina, Dwi Siswanta, Mustofa Mustofa, Naresh Kumar
• Format: Article
• Language: English
• Published: Universitas Gadjah Mada 2011-07-01
• Series: Indonesian Journal of Chemistry
• Subjects: fennel oil; chloromethylation; tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene; flattened partial cone; crown
• Online Access: https://jurnal.ugm.ac.id/ijc/article/view/21411
• ISSN: 1411-9420; 2460-1578

A research has been conducted to synthesize thiomethylated-C-4-methoxyphenylcalix[4]resorcinarene using fennel oil as a starting material. The synthesis was carried out in four steps i.e. (1) oxidation of anethole to yield p-anisaldehyde, (2) HCl-catalyzed condensation of p-anisaldehyde with resorcinol, (3) chloromethylation of C-4-methoxyphenylcalix[4]resorcinarene with paraformaldehyde and HCl in the presence of ZnCl2 to yield tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene, and (4) reaction of tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene with thiourea followed by hydrolysis with sodium hydroxide solution to yield tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene. The prepared compounds were characterized based on melting point, FT-IR, and NMR spectrometers. According to the analysis of 1H-NMR spectrometer, C-4-methoxyphenylcalix[4]resorcinarene and tetrakis-chloromethyl-C-4-methoxyphenylcalix[4]resorcinarene were observed in the chair or flattened partial cone conformation, while tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene tend to exist in the crown or cone conformation.