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

Triana Kusumaningsih (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)
Jumina Jumina (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281)
Dwi Siswanta (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281)
Mustofa Mustofa (Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Bulaksumur Yogyakarta 55281)

Indonesian Journal of Chemistry
Vol 10, No 1 (2010)

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.