1,3-Dichloro-5,5-dimethyl hydantoin and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide as efficient catalysts for the methoxymethylation of alcohols under solvent-free conditions

Document Type: Original Research Article

Authors

1 Payame Noor University, Hamedan

2 Faculty of Chemistry, Bu-Ali Sina University, P.O. Box 651783868, Hamedan, Iran

3 Department of Chemistry, Payame Noor University, 19395-4697 Tehran, I. R. of Iran

4 Department of Chemistry, Faculty of Science, Ayatollah ozma Boroujerdi University, Boroujerd, Iran

5 Young Researchers & Elites Club, Toyserkan Branch, Islamic Azad University, Toyserkan, Iran

Abstract

Methoxymethylation of a variety of alcohols was performed using formaldehyde dimethyl acetal in the presence of 1,3-dichloro-5,5-dimethyl hydantoin [DCDMH] and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide [PBNS] as catalysts at room temperature and under solvent-free conditions. Our experiments show that primary and secondary alcohols can be smoothly converted into the corresponding MOM-ethers in excellent yields. The methoxymethyl ethers (MOM-ethers) were obtained with good to excellent yields. 1,3-Dichloro-5,5-dimethyl hydantoin [DCDMH] and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide [PBNS] effectively catalyzed the methoxymethylation of alcohols with dimethoxymethane at ambient temperature. The notable advantages of this method are mild reaction conditions, high yields, cheapness, safety and eco-friendliness, and recyclability of the catalysts.

Graphical Abstract

1,3-Dichloro-5,5-dimethyl hydantoin and Poly N,N′-dibromo-N-ethyl naphthyl-2,7-disulfonamide as efficient catalysts for the methoxymethylation of alcohols under solvent-free conditions

Keywords

Main Subjects


[1] T.W. Greene, P.G.M. Wuts, Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991.

[2] Occupational Safety and Health Administration, U.S. Department of Labour, Federal Register, 1974, 39 (20), 3756.

[3] S. Gharaati, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, F. Kosari, Inorg. Chimica Acta, 2010, 363, 1995–2000.

[4] I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, A. Mirjafari, C.R. Chimie, 2011, 14, 568–579.

[5] M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork,

M. Khajehzadeh, F. Kosari, M. Araghi, Polyhedron, 2010, 29, 238–243.

[6] F. Shirini, M. Abedini, M. Shamsi-Sani, M. Seddighi, Iranian Journal of Catalysis, 2015, 5, 373-381.

[7] M.L. Kantam, P.L. Santhi, Synlett, 1993, 429-430.

[8] R.L. Danheiser, K.R. Romines, H. Koyama , S.K. Gee, C.R. Johnson,  J.R. Medich, Org. Synth., 1992, 71, 133.

[9] B.P. Bandgar, C.T. Hajare, P.P. Wadgaonkar, J. Chem.Res., (S), 1996, 90-91.

[10] T.S. Jin, J.J. Guo, Y. H. Yin, S.L. Zhang, T.S. Li, J. Chem. Res., (S), 2002, 188-189.

[11] T.S. Jin, T.S. Li, Y.T. Gao, Synth. Commun., 1998, 28, 837-841.

[12] H.K. Patney, Synlett, 1992, 567-568.

[13] B.F. Marcune, S. Karady, U.H. Dolling, T.J. Novak, J. Org. Chem., 1999, 64, 2446-2449.

[14] B. Karimi, L. Mamani, Tetrahedron Lett., 2003, 44, 6051-6053.

[15] K. Niknam, M.A. Zolfigol, A.  Khorramabadi,  R. Zare, M. Shayegh, Catal. Commun., 2006, 7, 494-498.

[16] M.A. Zolfigol, M. Shiri, Mendeleev Commun., 2005, 165-166.

[17] A. Khazaei, A.  Amini Manesh, Synthesis, 2005, 12, 1929-1931.

[18] A. Khazaei, A.  Amini Manesh, J. Chin. Chem. Soc., 2005, 52, 1017-1020.

[19] R. Ghorbani-Vaghei, M.A. Zolfigol, M. Chegeny, H. Vesis, Tetrahedron. Lett., 2006, 47, 4505-4508.

[20] A. Khazaei, S. Shahnaz, L. Roshani, M. Kazem-Rostami, Z. Abdolkarim, Letters in Organic Chemistry, 2014, 11, 159-167.