Synthesis of 1, 2-Aceanthrylenedione Catalyzed by Anhydrous AlCl3


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1,2-aceanthrylenedione was synthesized through the acylation reaction of anthracene and oxalyl chloride catalyzed by anhydrous AlCl3. The effects of various reaction conditions on the yield and selectivity of 1, 2-aceanthrylenedione were studied by GC analysis. The results show that the optimum synthesis conditions of the acylation reaction are as follows : the molar ratio of oxalyl chloride to anthracene being 1:2, the molar ratio of anhydrous AlCl3 to anthracene being 4:1, the reaction time being 5 h, the reaction temperature being 303k and the solvent of the reaction system being CS2. Under those conditions, the yield and selectivity of 1, 2-aceanthrylenedione is 83.8 % and 92.3% respectively. Pure 1, 2-aceanthrylenedione was prepared by extraction and recrystallation. The structure of 1, 2-aceanthrylenedione was identified by measure of melting point, GC/MS, FTIR and 1HNMR analyses.



Materials Science Forum (Volumes 561-565)

Main Theme:

Edited by:

Young Won Chang, Nack J. Kim and Chong Soo Lee




C. Y. Zhang et al., "Synthesis of 1, 2-Aceanthrylenedione Catalyzed by Anhydrous AlCl3", Materials Science Forum, Vols. 561-565, pp. 683-686, 2007

Online since:

October 2007




[1] G.A. Olah, Friedel-Crafts and Related Reactions, Wiley/Interscience, New York, vols. I-IV, 1963-(1964).

[2] Freese U , Heinrich F , Roessner F.J. Catal Today , vol 49 (1999) ,P. 237.

[3] Heaney, H. ; Trost, B. M.; Fleming, I., Eds.; In Comprehensive Organic Synthesis; Pergamon Press: Oxford, Vol. 2( 1991 ), P. 733-752.

[4] Ravi P Singh, Rajesh M Kamble, Kusum L Chandra.J. Tetrahedron. vol. 57(2001),P. 241-247.

[5] Christopher Hardacre, Suhas P. Katdare, journal of catalysis. Vol. 227(2004),P. 44-52.

[6] Zhong-Wei Wang , Li-Sheng Wang .J. applied catalysis A: General Vol. 262(2004),P. 101-104.

[7] Carlos Gutierrez Blanco, Dolores Casal Banciella.J. Journal of Molecular Catalysis A: Chemical Vol. 253 (2006),P. 203-206.


[8] ChristopherJ. Adams, Martyn J. Earle, Glyn Roberts Kenneth R. Seddon .J. Chem. Commun. Vol. 19(1998),P. (2097).

[9] Habib Firouzabadi, Nasser Iranpoor, Farhad Nowrouzi .J. Tetrahedron Vol. 60(2004),P. 10843.