SYNTHESIS of 3.4-METHYLENEDIOXYPHENYL-2-PROPANONE from SAFROLE

Hanoch J Sohilait; Hardjono Sastrohamidjojo; Sabirin Matsjeh; J Stuart Grossert

doi:10.22146/ijc.21941

SYNTHESIS of 3.4-METHYLENEDIOXYPHENYL-2-PROPANONE from SAFROLE

https://doi.org/10.22146/ijc.21941

Hanoch J Sohilait^(1*), Hardjono Sastrohamidjojo⁽²⁾, Sabirin Matsjeh⁽³⁾, J Stuart Grossert⁽⁴⁾

(1) Chemistry Department, Pattimura University, Ambon
(2) Chemistry Department, Gadjah Mada University, Yogyakarta
(3) Chemistry Department, Gadjah Mada University, Yogyakarta
(4) Department of Chemistry, Dalhousie University,Halifax, Nova Scotia
(*) Corresponding Author

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.

Keywords

3.4-methylenedioxyphenyl-2-propanone; safrole

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References

[1] Anwar, C; 1994, The Conversion of Eugenol into More Valuable Substances, Disertasi Universitas Gadjah Mada, Yogyakarta.

[2] Fuhrhop, J; and Penzlin, G, 1994; Organic Synthesis, Concepts, Methods, Starting materials, second edition; VCH Weinheim; New York.

[3] French, L.G, 1995; The Sassafras Tree and Designer Drugs; J. Chem. Educ., Vol.72, No. 6, 484- 491.

[4] Kleinfelter,D.C; Schleyer, P.von.R, 1973, Organic Synthesis, Volume 5, John Wiley and Sons, New York

[5] Brown, H.C and Geoghegen, Jr, P.J, 1970; The Oxymercuration-Demercuration of Representative Olefins in an Aqueous System. A Convenient Mild Procedure for Markovnikov Hydration of the Carbon-Carbon Double Bond, J.Org. Chem., Vol.35, No.6, 1844-1850

[6] Brown, H.C and Lynch, G.J, 1981; Oxymercuration-Demercuration of Methoxy-, Hydroxy-, and Acetoxy-Substituted Alkenes; J. Org. Chem., vol.46, No. 3, 531-538

[7] Corey, E,J and Suggs, J.W, 1975; Pyridinium chlorochromate An Efficient Reagent for Oxidation of Primary and Secondary Alkohols to Carbonyl Compounds; Tetrahedron letters, No.31, 2647-2650.

DOI: https://doi.org/10.22146/ijc.21941