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Mustofa Mustofa
Department of Pharmacology and Toxicology, Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta
Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS 7-HYDROXY-3’,4’-DIMETHOXYISOFLAVON FROM EUGENOL Andi Hairil Alimuddin; Muhammad Idham Darussalam Mardjan; Sabirin Matsjeh; Chairil Anwar; Mustofa Mustofa; Eti Nurwening Sholikhah
Indonesian Journal of Chemistry Vol 11, No 2 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (233.66 KB) | DOI: 10.22146/ijc.21404

Abstract

Eugenol from the isolation of clove leaves oil had been utilized in the synthesis of 7-hydroxy-3',4'-dimethoxy-isoflavone based on deoxybenzoin intermediate. The raw material was firstly converted into methyleugenol using DMS (89.87%). Secondly, methyl eugenol was oxidized using KMnO4 to produce 3,4-dimethoxybenzyl carboxylic acid (21%). Friedel-Craft acylation of it with recorcinol produced 3,4-dimethoxybenzyl-2',4'-dihydroxyphenyl ketone (deoxybenzoin intermediate) in 78% yield. Eventually, cyclization of the intermediate with reagents of BF3.OEt2/DMF/POCl3 yielded 7-hydroxy-3',4'-isoflavone in 85% yield.
SYNTHESIS OF THIOMETHYLATED CALIX[4]RESORCINARENE BASED ON FENNEL OIL VIA CHLOROMETHYLATION Suryadi Budi Utomo; Jumina Jumina; Dwi Siswanta; Mustofa Mustofa; Naresh Kumar
Indonesian Journal of Chemistry Vol 11, No 1 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (435.978 KB) | DOI: 10.22146/ijc.21411

Abstract

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.
SYNTHESIS OF POLYPROPYLCALIX[6]ARENE FROM p-t-BUTYLPHENOL AS ADSORBENT FOR Cr(III) METAL ION Susy Yunita Prabawati; Jumina Jumina; Sri Juari Santosa; Mustofa Mustofa
Indonesian Journal of Chemistry Vol 11, No 1 (2011)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (294.13 KB) | DOI: 10.22146/ijc.21417

Abstract

A study has been conducted to synthesize a novel polypropylcalix[6]arene polymer using p-t-butylphenol as a starting material. It was of interest to investigate the capability of the polymer with a tunnel-like structure, as adsorbent to trap the heavy metal cation such as Cr3+. The synthesis was carried out in several steps i.e (1) formation of p-t-butylcalix[6]arene from p-t-butylphenol as a starting material, (2) treatment of p-t-butylcalix[6]arene with 4.95 equivalents of allyl bromide under  alkaline conditions to yield p-t-butyl-37,40-diallyloxy-38,39,41,42-tetra-hydroxy-calix[6]arene, and (3) polymerization of p-t-butyl-37,40-diallyloxy-38,39,41,42-tetrahydroxycalix[6]arene by treatment with concentrated sulfuric acid to yield polypropyl-calix[6]arene. The application of polypropylcalix[6]arene for trapping Cr(III) was investigated by stirring the suspension of calixarene under variation of pH, time, and adsorbent mass. IR and 1H NMR spectra, showed that two allyl groups had been incorporated to the lower rim of the p-t-butylcalix[6]arene and the polymer was obtained as brownish green crystals with the melting point of 108-110 °C. The study also showed that the polypropylcalix[6]arene was able to trap Cr(III) cation. The optimum adsorption conditions were achieved at pH 5, contact time 60 min and concentration 12 mg/l for every 0,008 g of polymer.
Co-Authors Andi Hairil Alimuddin Chairil Anwar Dwi Siswanta Eti Nurwening Sholikhah Jumina Jumina Jumina Jumina Muhammad Idham Darussalam Mardjan Naresh Kumar Sabirin Matsjeh Sri Juari Santosa Suryadi Budi Utomo Susy Yunita Prabawati