SYNTHESIS OF TETRA-p-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-p-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM p-t-BUTYLPHENOL

https://doi.org/10.22146/ijc.21491

Triana Kusumaningsih(1*), Jumina Jumina(2), Dwi Siswanta(3), Mustofa Mustofa(4)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Surakarta 57126; Postgraduate Student of Chemistry Department, Faculty of Mathematic and Natural Sciences, Universitas Gadjah Mada
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281
(4) Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281
(*) Corresponding Author

Abstract


A research has been conducted to synthesize tetra-p-propenyltetraestercalix[4]arene and tetra-p-propenyltetracarboxylicacidcalix[4] arene using p-t-butylphenol as a starting material. The synthesis was carried out in following stages, i.e (1) synthesis of p-t-butylcalix[4]arene from p-t-butylphenol, (2) debutylation of p-t-butylcalix[4]arene, (3) tetraallilation of 25,26,27,28-tetrahydroxycalix[4]arene with NaH and allilbromida in dry tetrahydrofuran, (4) Claissen rearrangement of 25,26,27,28-tetrapropenyloxycalix[4]arene, (5) esterification of tetra-p-propenyltetrahydroxycalix[4]arene, (6) hydrolisis of tetra-p-propenyltetraestercalix[4]arene. The all structures of products were observed by means of melting point, FTIR, and 1H-NMR spectrometers. Tetra-p-propenyltetraestercalix[4]arene compound was obtained as yellow liquid product in 55.08% yield. Tetra-p-propenyltetracarboxylicacidcalix[4]arene compound was obtained as white solid product with the melting point 135-137 °C at decomposed and in 70.05% yield.


Keywords


calix[4]arene; Claissen rearrangement; esterification; hydrolisis

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DOI: https://doi.org/10.22146/ijc.21491

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