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J Stuart Grossert
Department of Chemistry, Dalhousie University,Halifax, Nova Scotia
Chemical Engineering, Chemistry & Bioengineering Chemistry

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SYNTHESIS of 3.4-METHYLENEDIOXYPHENYL-2-PROPANONE from SAFROLE Hanoch J Sohilait; Hardjono Sastrohamidjojo; Sabirin Matsjeh; J Stuart Grossert
Indonesian Journal of Chemistry Vol 1, No 3 (2001)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (69.382 KB) | DOI: 10.22146/ijc.21941

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.
Co-Authors Hanoch J Sohilait Hardjono Sastrohamidjojo Sabirin Matsjeh