Indonesian Journal of Chemistry
Vol 1, No 3 (2001)

SYNTHESIS of 3.4-METHYLENEDIOXYPHENYL-2-PROPANONE from SAFROLE

Hanoch J Sohilait (Chemistry Department, Pattimura University, Ambon)
Hardjono Sastrohamidjojo (Chemistry Department, Gadjah Mada University, Yogyakarta)
Sabirin Matsjeh (Chemistry Department, Gadjah Mada University, Yogyakarta)
J Stuart Grossert (Department of Chemistry, Dalhousie University,Halifax, Nova Scotia)



Article Info

Publish Date
05 Jun 2010

Abstract

The Synthesis of 3.4-methylenedioxyphenyl-2-propanone from safrole has been achieved through conversion of allyl group to secondary alcohol, followed by oxidation with pyridinium chlorochromate(PCC).  The secondary alcohol has been achieved by two methods. The first method was formic acid adition reaction, followed by hydrolysis in aqueous ethanolic solution of potassium hydroxide.  The second method was the oxymercuration-demercuration reaction of safrole. The addition reaction of safrole with formic acid yield safrylformate (34,70%). The hydrolysis of safrylformate with 3M KOH produced safrylalchohol (73,29%). The oxymercuration-demercuration reaction of safrole with Hg(OAc)2-NaBH4 gave (74,37%) of safrylalcohol.  The oxidation of safryalcohol with PCC gave 3.4-methylenedioxyphenyl-2-propanone as a main target in 71,83%. The structure elucidations 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 ...