SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION
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 resorci...
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doaj-880c45d0cef042b189549e9a02cce5cb2020-11-24T22:00:28ZengUniversitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782011-07-011111810.22146/ijc.2141114509SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATIONSuryadi Budi Utomo0Jumina Jumina1Dwi Siswanta2Mustofa Mustofa3Naresh Kumar4Chemical Education Study Program, PMIPA FKIP, Sebelas Maret University, SurakartaChemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, YogyakartaChemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, YogyakartaDepartment of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, YogyakartaSchool of Chemistry, Faculty of Science, University of New South Wales, Sydney, NSW 2052A 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.https://jurnal.ugm.ac.id/ijc/article/view/21411fennel oilchloromethylationtetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinareneflattened partial conecrown |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Suryadi Budi Utomo Jumina Jumina Dwi Siswanta Mustofa Mustofa Naresh Kumar |
spellingShingle |
Suryadi Budi Utomo Jumina Jumina Dwi Siswanta Mustofa Mustofa Naresh Kumar SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION Indonesian Journal of Chemistry fennel oil chloromethylation tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene flattened partial cone crown |
author_facet |
Suryadi Budi Utomo Jumina Jumina Dwi Siswanta Mustofa Mustofa Naresh Kumar |
author_sort |
Suryadi Budi Utomo |
title |
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION |
title_short |
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION |
title_full |
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION |
title_fullStr |
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION |
title_full_unstemmed |
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION |
title_sort |
synthesis of thiomethylated calix[4]resorcinarene based on fennel oil via chloromethylation |
publisher |
Universitas Gadjah Mada |
series |
Indonesian Journal of Chemistry |
issn |
1411-9420 2460-1578 |
publishDate |
2011-07-01 |
description |
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. |
topic |
fennel oil chloromethylation tetrakis-thiomethyl-C-4-methoxyphenylcalix[4]resorcinarene flattened partial cone crown |
url |
https://jurnal.ugm.ac.id/ijc/article/view/21411 |
work_keys_str_mv |
AT suryadibudiutomo synthesisofthiomethylatedcalix4resorcinarenebasedonfenneloilviachloromethylation AT juminajumina synthesisofthiomethylatedcalix4resorcinarenebasedonfenneloilviachloromethylation AT dwisiswanta synthesisofthiomethylatedcalix4resorcinarenebasedonfenneloilviachloromethylation AT mustofamustofa synthesisofthiomethylatedcalix4resorcinarenebasedonfenneloilviachloromethylation AT nareshkumar synthesisofthiomethylatedcalix4resorcinarenebasedonfenneloilviachloromethylation |
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