SYNTHESIS OF SAFRYL KETONE FROM SAFROLE

https://doi.org/10.22146/ijc.21874

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

(1) Jurusan Kimia, FMIPA Universitas Pattimura, Ambon
(2) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(3) Chemistry Department, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Yogyakarta
(4) Department of Chemistry, Dalhousie University, Halifax, Nova Scotia
(*) Corresponding Author

Abstract


Synthesis of safryl ketone from safrole has been achieved through conversion of allyl group to secondary alcohol, followed by oxidation with PCC-Al2O3. The oxymecuration-demercuration reaction of safrole with HgSO4-NaBH4 yields safryl alcohol (66.38%) and the oxidation of safryl alcohol with PCC-Al2O3 yields safryl ketone (62.92%). The structure elucidation of these products was conducted using Fourier Transformed Infra Red Spectroscopy (FTIR), Proton-Nuclear Magnetic Resonance (1H-NMR) and Mass Spectroscopy (MS).


Keywords


safryl ketone; safrole

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References

[1] French, L.G, 1995, J. Chem. Educ., Vol 72, No.6, 484-491.

[2] Sohilait, H. J, Sastrohamidjojo, H, Matsjeh, S dan Grossert, J.S, 2001, Indo. J. Chem., 1, 3, 145-148.

[3] Brown, H.C and Lynch, G.J, 1981, J. Org. Chem, Vol. 46, No. 3, 531-538.

[4] Brown, H.C and Geoghegen, Jr, P.J, 1970, J. Org. Chem, Vol. 6, 1844-1850.

[5] Corey,E.J and Suggs, J.W, 1975, tetrahedron letters, No.31, 2647-2650.

[6] Hudickly, M, 1990, Oxidation in Organic Chemistry; ACS Monograph 186, Washington, DC



DOI: https://doi.org/10.22146/ijc.21874

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