Preparation of α-damascone

• Autorzy: Hu Junyi , Guo Aiqiang , Xu Yingqian , Pan Changsheng , Wei Xingfu , Wang Longlong , Xiao Guoyong

Identyfikatory

DOI

10.2478/pjct-2019-0009

• Języki publikacji: EN

Abstrakty

EN

α-Damascone is widely used in perfumes. However, the manufacture of α-damascone remains challenging owing to the limitations of current production processes. Herein, α-damascone was successfully synthesized from α-ionone using a new route involving only four steps, namely oximization, epoxidation, dehydration, and reduction. The total yield was 54.9% with a final chemical purity of 97% (by GC). Only water, cyclohexane, and ethanol were used in the reactions except in the purification step, and all solvents could be recycled. The structures of the intermediates and target compound were identified by ¹H NMR and  ¹³C NMR analyses and MS experiments. This route is a simple and successful method for the industrial preparation of α-damascone.

Słowa kluczowe

EN

α-damascone; α-ionone; preparation

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2019
• Tom: Vol. 21, nr 1
• Strony: 50--51
• Opis fizyczny: Bibliogr. 10 poz., rys.

Twórcy

autor

Hu Junyi

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

autor

Guo Aiqiang

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

autor

Xu Yingqian

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

autor

Pan Changsheng

• Jijia Geen Bilding Tchnology co., LTD, Liaoning Anshan, 114051, P. R. China

autor

Wei Xingfu

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

autor

Wang Longlong

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

autor

Xiao Guoyong

• University of Science and Technology Liaoning, School of Chemical Engineering, Liaoning Anshan, 114051, P. R. China

Bibliografia

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• 2. Kenji, M. & Masayasu, A. (1993) Synthesis of (S)-α-damascone. Tetrahedron . 49(9), 1871–1878. DOI: 10.1016/S0040-4020(01)80543-3.
• 3. Werkhoff, P., Bretschneider, W. & Güntert, M., et al . (1991) Chirospecific analysis in flavor and essential oil chemistry Part B. Direct enantiomer resolution of frans-α-ionone and trans-α-damascone by inclusion gas chromatography. Z. Lebensm.--Unters. Forsch. 192(2), 111–115. DOI: 10.1007/BF01202622.
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• 5. Stefano, S. & Claudio, F. (2006) Synthesis of the enantiomeric forms of α- and γ-damascone starting from commercial racemic α-ionone. Tetrahedron Asymmetry . 17(10), 1573–1580. DOI: 10.1016/j.tetasy.2006.05.024.
• 6. Boulin, B., Taran, M. & Arreguy-San, M.B., et al . (2007) New Preparation Methods for α-Damascone, γ-Damascone, and β-Damascenone using Pyronenes. Communications. 37(15), 2579–2591. DOI: 10.1080/00397910701462898.
• 7. Luis, A.S. & Jean, L.L. (1992) A new synthesis of α- and β-damascones from the ionones. J. Org. Chem ., 57(9), 2757–2760. DOI: 10.1021/jo00035a045.
• 8. Gosselin, P. (1988) Acid catalyzed hydrolysis of a dienyl sulfide. Application to the synthesis of α-damascone. Tetrahedron , 44(7), 1979–1990. DOI: 10.1002/chin.198831288.
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• 10. Fioroni, G., Fringuelli, F. & Pizzo, F., et al . (2003) Epoxidation of α, β,-unsaturated ketones in water. An environmentally benign protocol. Green Chem. 5(4), 425–428. DOI: 10.1039/b303883a.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2019).