SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL
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,...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Department of Chemistry, Universitas Gadjah Mada
2010-06-01
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| Series: | Indonesian Journal of Chemistry |
| Online Access: | https://jurnal.ugm.ac.id/ijc/article/view/21491 |
| Summary: | 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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| ISSN: | 1411-9420 2460-1578 |