Friedel–Crafts synthesis of triarylmethanes over 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate under solvent-free conditions

Document Type: Articles

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran

2 Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran

3 Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad, 6541835583, Iran

Abstract

Friedel–Crafts synthesis of triarylmethanes over 3-methyl-1-sulfonic acid imidazolium tetrachloroaluminate under green conditions:In this work, Friedel–Crafts (FC) alkylation of various arenes with aromatic aldehydes catalyzed by 3-methyl-1-sulfonic acid imidazoliumtetrachloroaluminate {[Msim]AlCl4}, as a green catalyst, to prepare triarylmethanes (TAMs) has been carried out. Some aromatic aldehydes were reacted with arenes containing electron-donor substitutions such as anisole, veratrole, phenols, indole and 2-naphtole under solvent-free conditions. The catalyst was recovered and reused successfully for four times. Simple methodology, easy work up, solvent-free condition and excellent yields are some advantages of this work.The promising points for the presented method are high yield, green reaction profile, easier work up and simplicity which make it a useful process for the preparation of various triarylmethanes

Keywords


[1] N. Mibu, K. Sumoto, Chem. Pharm. Bull. 48 (2000) 1810-1813.
[2] M. Ota, S. Otani, K. Kobayashi, M. Igarashi, Mol. Cryst. Liq. Cryst. 176 (2006) 99-108.
[3] H. Li, J. Yang, Y. Liu, Y. Li, J. Org. Chem. 74 (2009) 6797-6801.
[4] J.Y. Yu, R. Kuwano, Org. Lett. 10 (2008) 973-976.
[5] I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, K. Mohammadiannejad-Abbasabadi, M.A. Zolfigol, C. R. Chim. 14 (2011) 934-943.
[6] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A: Gen. 400 (2011)
70-81.
[7] M. A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, H. G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem- Rostami, J. Org. Chem. 77 (2012) 3640-3645.
[8] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Zare, S. B. Azimi, Z. Asgari, A. Hasaninejad; C.R. Chim. 15 (2012) 719-736.
[9] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Z. Asgari, A. Hasaninejad, Sci. Iran. Trans. C. 18 (2012) 1365-1371.
[10] M. A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Org. Prep. Proced. Int. 42 (2010) 95-102.
[11] M. A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc. 7 (2010) 646-651.
[12] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, Sci. Iran., Trans. C. 17 (2010) 31-36.
[13] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, E. Ghaemi, V. Khakyzadeh, Z. Asgari, A. Hasaninejad, Sci. Iran. Trans. C. 18 (2011) 1365-1371.
[14] A. Zare, T. Yousofi, A.R. Moosavi-Zare, RSC. Adv. 2 (2012) 7988-7991.
[15] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, Z. Asgari, M. Shekouhy, A. Zare, A. Hasaninejad, RSC. Adv. 2 (2012) 8010-8013.
[16] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, G. Chehardoli, F. Derakhshan-Panah, A. Zare, O. Khaledian, Sci. Iran., Trans. C. 19 (2012) 1584-1590.
[17] A.R. Moosavi-Zare, Z. Naz, Iran. Chem. Commun. 2 (2014) 34-38.