Document Type: Original Research Article

Authors

Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran

10.30473/icc.2020.50278.1643

Abstract

The reaction of 2-naphthol and also para-substituted phenols with glyoxal in presence of choline chloride: 2 ZnCl2 [ChCl: 2ZnCl2], a deep eutectic solvent (DES), as a green catalyst was studied. The amount of catalyst, solvent type, temperature, and time on the yield of reaction were investigated. It was found that the optimal condition included 10% mol ratio of catalyst (mol percentage of DES to glyoxal), solvent-free condition (60 °C) and the time about one hour. Under these conditions, products are obtained in good yield (80%). The products were characterized on the basis of FT-IR, 1H-NMR, 13C-NMR spectra and comparison of melting point with authentic sample. The NMR spectra indicated that of the two probable isomers with an acetal and ether structure; the aforementioned reaction, regioselectively, furnished compounds with acetal linkage, rather than ether.

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[1] A. Chwala, W. Bartek, Monatsch., 1951, 82, 652-653.

[2] P. Maravingna, J. Polym. Sci., Polym. Chem. Ed., 1988, 26, 2475-2485.

[3] O. Anselimo, Ber., 1908, 41, 621-623.

[4] A. Rosenthal, A. Zaionchkovsky, Can. J. Chem., 1960, 38, 2277-2278.

[5] E.C.M. Coxworth,  Can. J. Chem., 1967, 45, 1777-1784.

[6] A. Rahmatpour, J. Heterocyclic Chem., 2010, 47, 1011-1016.

[7] A.A. Tunca, N. Talinli, A. Akar, Tetrahedron, 1995, 51, 2109-2116.

[8] D. Ergunes, Z. Kokce, O. Sirkecioglu, N. Talinli, Rev. Roum. Chim., 2010, 55, 455-458.

[9] A. Banihashemi, A. Rahmatpour, Tetrahedron, 1999, 55, 7271-7278.

[10] R. Riemschneider, W. Cohnen, Chem. Ber., 1958, 91, 2600-2604.

[11] R. Riemschneider, I. Ahrlé, W. Cohnen, E. Heilmann, Chem. Ber., 1959, 92, 900-909.

[12] R. Riemschneider, W. Cohnen, Chem. Ber., 1957, 90, 2720-2727.

[13] T. Kito, K. Yoshinaga, M. Yamaye, H. Mizobe, J. Org. Chem., 1991, 56, 3336-3339.

[14] A. Banihashemi, A. Rahmatpour, Eur. Polym. J., 1998, 34, 1809-1815.

[15] J. Cretenoud, B. Özen, T. Schmaltz, D. Görl, A. Fabrizio, C. Corminboeuf, F. Fadaei, R. Scopelliti, H. Frauenrath, Polym. Chem., 2017, 8, 2197-2209.

[16] A. Banihashemi, B. Pourabbas, Iran. Polym. J., 1996, 5, 145-151.

[17] H. Namazi, A. Assadpour, B. Pourabbas, A. Entezami, J. Appl. Polym. Sci., 2001, 81, 505–511.

[18] K. Ghandi, Green Sustain. Chem., 2014, 4, 44-53.

[19] A.P. Abbot, G. Capper, D.L. Davies, R.K. Rasheed and V. Tambyrajah, Chem. Commun., 2003, 1, 70-71.

[20] E.L. Smith, A.P. Abbott, K.S. Ryder, Chem. Rev., 2014, 114, 11060–11082.

[21] A.P. Abbott, G. Capper, D.L. Davies, H.L. Munro, R.K. Rasheed, V. Tambyrajah, Chem. Commun., 2001, 19, 2010-2011.

[22] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, Inorg. Chem., 2004, 43, 3447-3452.

[23] A. Hiremathad, M.R. Patil, K.R. Chethana, K. Chand, M.A. Santos, R.S. Keri, RSC Adv., 2015, 5, 96809-96828.

[24] K. Chand, Rajeshwaria, A. Hiremathad, M. Singh, M.A. Santos, R.S. Keri, Pharmacol. Rep., 2017, 69, 281-295.

[25] S. Millefiori, A. Alparone, A. Millefiori, J. Heterocyclic Chem., 1997, 34, 195-201.

[26] M.C. Venuti, Synthesis, 1982, 1, 61-63.

[27] M. Nanbu, K. Momonoi, S. Oguro, Y. Kawase, Bull. Chem. Soc. Jpn., 1975, 48, 3421-3422.