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Hardjono Sastrohamidjojo
Department of Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara Yogyakarta
Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS OF ANALOG L-α-METIL-DOPA FROM EUGENOL Hanoch J Sohilait; Hardjono Sastrohamidjojo; Sabirin Matsjeh; J Stuart Grossert
Indonesian Journal of Chemistry Vol 5, No 3 (2005)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (217.346 KB) | DOI: 10.22146/ijc.21788

Abstract

Synthesis of analog L-α-metil-Dopa from eugenol has been achieved through conversion of allyl group to ketone, followed by reaction with NH3 and KCN and by hydrolisis. The addition reaction of methyleugenol with formic acid yield methyleugenyl formate (60,69%). The hydrolis of methyileugenylformate with KOH in aqaueous-ethanolic solution produced methyleugenyl alcohol (73,68%). The oxidation of methyleugenyl alcohol with PCC yield methyleugenyl ketone (67,71%). The reaction of methyleugenyl ketone with NH3 and KCN yield D,L-α-amino-α-(3,4-dimetoxybenzyl) propionitril (84,14%). The hydrolisis of D,L-α-amino-α-(3,4-dimetoxybenzyl) propionitril with concentrated hydrochloric acid gave Analog L-α-metil-Dopa as a main target (91,98%). The structure elucidation of these products were analyzed by FTIR, 1H-NMR, 13C-NMR and MS
Co-Authors Hanoch J Sohilait J Stuart Grossert Sabirin Matsjeh