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M Muchalal
Chemistry Department, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Yogyakarta
Chemical Engineering, Chemistry & Bioengineering Chemistry

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ISOLATION AND IDENTIFICATION OF MAIN AND SIDE PRODUCTS FROM ADDITION REACTION OF CARYOPHYLLENE OXIDE BY FORMIC ACID M Muchalal; Trisulistyaningsih Rahayu
Indonesian Journal of Chemistry Vol 2, No 3 (2002)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (133.557 KB) | DOI: 10.22146/ijc.21910

Abstract

Main and side products from reaction of caryophyllene oxide and formic acid have been isolated using column chromatography with silica gel 60 G as stationary phase and n-hexane : ethyl acetat (9:1, v/v) as mobile phase. The first and second fraction were analyzed using infrared spectrophotometer, gas chromatography, and gas chromatography-mass spectrometer. Caryophyllene formiate as a main product was found in the first fraction. The side product that had been identified were 4,10,10-trimethyl-7-methylenebicyclo[6,2,0]decane-4-carbaldehyde, 2-(9-hydroxy-4,4,8 trimethyltricyclo[6,3,1,01,5]dodecyl)metanoate, clovanediol,4,11,11-trimethyl-8 methylene-3-bicyclo-[7,2,0]-undecen-5-ol,2,5-(6,10,10 imethyltricyclo[7,2,1,01,9]dodecyl)metanedioat, and derivative of caryophylleneformiate.
A STUDY OF THE SYNTHESIS OF VERATRYL CYANIDE REQUIRED AS AN INTERMEDIATE FOR THE PREPARATION OF C-9154 ANTIBIOTIC DERIVATIVE FROM VANILIN Ila Rosilawati; Jumina Jumina; M Muchalal
Indonesian Journal of Chemistry Vol 2, No 2 (2002)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (104.191 KB) | DOI: 10.22146/ijc.21925

Abstract

The synthesis of veratryl cyanide [1-(3,4-dimethoxy phenyl acetonitril] required as an intermediate for the preparation of C-9154 antibiotic derivative was carried out. The starting material used was vanilin, while the reaction steps consisted of (1) methylation of vanilin, (2) reduction of veratraldehyde, (3) synthesis of veratryl bromide, and (4) treatment of this bromide with KCN. The analysis of the products was carried out using IR, 1H NMR and GC-MS spectrophotometers.            The methylation of vanilin was conducted using dimethylsulfate and NaOH at 100  oC for 2 hours to give 79.3% yield of veratraldehyde. The reduction of veratraldehyde with LiBH4 in ethanol - THF mixture (1:1 v/v) at reflux for 4 hours afforded veratryl alcohol in 85.3% yield. This veratryl alcohol was treated with red phosphorous and Br2 in CCl4 at 60 oC for 2 hours to give 1-(2-bromo-4,5-dimethoxy)-phenyl bromomethane in 67.4% yield, instead of the desired veratryl bromide [1-3,4-dimethoxy)-phenyl bromomethane]. This benzyl bromide derivative was then treated with KCN in the presence of tween 80 as a phase catalyst transsfer in benzene-water solvent system at reflux for 2 hours to yield 1-(2-bromo-4,5-dimethoxy)phenyl acetonitril in 58.5%.
Co-Authors Ila Rosilawati Jumina Jumina Trisulistyaningsih Rahayu