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,...
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| Format: | Article |
| Language: | English |
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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 |
| _version_ | 1818925100584402944 |
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| author | Triana Kusumaningsih Jumina Jumina Dwi Siswanta Mustofa Mustofa |
| author_facet | Triana Kusumaningsih Jumina Jumina Dwi Siswanta Mustofa Mustofa |
| author_sort | Triana Kusumaningsih |
| collection | DOAJ |
| description | 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 |
| first_indexed | 2024-12-20T02:35:51Z |
| format | Article |
| id | doaj.art-02405be9fc7c48f296b1708dd4b6d674 |
| institution | Directory Open Access Journal |
| issn | 1411-9420 2460-1578 |
| language | English |
| last_indexed | 2024-12-20T02:35:51Z |
| publishDate | 2010-06-01 |
| publisher | Department of Chemistry, Universitas Gadjah Mada |
| record_format | Article |
| series | Indonesian Journal of Chemistry |
| spelling | doaj.art-02405be9fc7c48f296b1708dd4b6d6742022-12-21T19:56:27ZengDepartment of Chemistry, Universitas Gadjah MadaIndonesian Journal of Chemistry1411-94202460-15782010-06-0110112212610.22146/ijc.2149114589SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOLTriana Kusumaningsih0Jumina Jumina1Dwi Siswanta2Mustofa Mustofa3Department 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 MadaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281A 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, hydrolisishttps://jurnal.ugm.ac.id/ijc/article/view/21491 |
| spellingShingle | Triana Kusumaningsih Jumina Jumina Dwi Siswanta Mustofa Mustofa SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL Indonesian Journal of Chemistry |
| title | SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL |
| title_full | SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL |
| title_fullStr | SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL |
| title_full_unstemmed | SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL |
| title_short | SYNTHESIS OF TETRA-<i>p</i>-PROPENYLTETRAESTERCALIX[4]ARENE AND TETRA-<i>p</i>-PROPENYLTETRACARBOXYLICACIDCALIX[4]ARENE FROM <i>p-t</i>-BUTYLPHENOL |
| title_sort | synthesis of tetra i p i propenyltetraestercalix 4 arene and tetra i p i propenyltetracarboxylicacidcalix 4 arene from i p t i butylphenol |
| url | https://jurnal.ugm.ac.id/ijc/article/view/21491 |
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