Indonesian Journal of Chemistry
Vol 5, No 3 (2005)

SYNTHESIS OF ANALOG L-α-METIL-DOPA FROM EUGENOL

Hanoch J Sohilait (epartment of Chemistry, Faculty of Mathematics and Natural Sciences Pattimura University, Kampus PGSD, Ambon)
Hardjono Sastrohamidjojo (Department of Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara Yogyakarta)
Sabirin Matsjeh (Department of Chemistry, Faculty of Mathematics and Natural Sciences Gadjah Mada University, Sekip Utara Yogyakarta)
J Stuart Grossert (epartment of Chemistry, Dalhousie University Nova Scotia, Canada)



Article Info

Publish Date
15 Jun 2010

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

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Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...