Abstract
Different primary, secondary, and tertiary alcohols were efficiently converted to their corresponding methoxymethyl ethers with formaldehyde dimethyl acetal in the presence of catalytic amounts of ZrO(OTf)2 at room temperature. Phenols were also methoxymethylated by this catalytic system. Advantages of using this catalytic system are the short reaction times, easy catalyst preparation, high product yield, solvent-free conditions, applicability for both alcohols and phenols, and reusability of the catalyst.
Graphical abstract
Similar content being viewed by others
References
Schelhaas M, Waldmann H (1996) Angew Chem Int Ed 35:2056
Greene TW, Wuts PGM (1991) Protective groups in organic synthesis. Wiley, New York
Kocienski PJ (1994) Protecting groups. Thieme, Stuttgart
Gras JL, Chang YYKW, Guerin A (1985) Synthesis 74
Fuji K, Nakano S, Fujita E (1975) Synthesis 276
Yarley JP, Fletcher H (1976) Synthesis 244
Olah GA, Husain A, Gupta BGB, Narang SC (1981) Synthesis 471
Olah GA, Husain A, Narang SC (1983) Synthesis 896
Danheiser RL, Romines KR, Koyama H, Gee SK, Johnson CR, Medich JR (1992) Org Synth 71:133
Bandgar BP, Hajare CT, Wadgaonkar PP (1996) J Chem Res (S) 90
Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork V, Khajehzadeh M, Kosari F, Araghi M (2010) Polyhedron 29:238
Jin TS, Li TS, Gao YT (1998) Synth Commun 28:837
Lin CH, Wan YM, Huang YM (2003) Catal Lett 87:253
Niknam K, Zolfigol MA, Khorramabadi-Zad A, Zare R, Shayegh M (2006) Catal Commun 7:494
Karimi B, Ma’mani L (2003) Tetrahedron Lett 44:6051
Sreedhar B, Swapna V, Sridhar C (2005) Catal Commun 6:293
Sharma GVM, Reddy KL, Lakshmi PS, Krishna PR (2004) Tetrahedron Lett 45:9229
Kantam ML, Santhi PL (1993) Synlett 429
Zolfigol MA, Shiri M (2005) Mendeleev Commun 165:165
Patney HK (1992) Synlett 567
Jin TS, Guo JJ, Yin YH, Zhang SL, Li TS (2002) J Chem Res (S) 188
Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Mirjafari A (2008) Can J Chem 86:831
Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Mirkhani V, Mirjafari A (2008) Polyhedron 27:2612
Firouzabadi H, Jafarpour M (2008) J Iran Chem Soc 5:159
Bora U (2003) Synlett 1073
Heine HW, Cottle DL, Van Mater HL (1946) J Am Chem Soc 68:524
Evans DA, Chapman KT, Bisaha J (1988) J Am Chem Soc 110:1238
Smitha G, Patnaik S, Reddy CS (2005) Synthesis 711
Firouzabadi H, Iranpoor N, Karimi B (1999) Synlett 319
Firouzabadi H, Iranpoor N, Karimi B (1999) Synlett 321
Moghadam M, Mohammadpoor-Baltork I, Tangestaninejad S, Mirkhani V, Yazdani P, Ghorjipoor S (2009) Heteroatom Chem 20:131
Mohammadpoor-Baltork I, Khosropour AR, Hojati SF (2007) Catal Commun 8:200
Mirkhani V, Mohammadpoor-Baltork I, Moghadam M, Tangestaninejad S, Abdollahi-Alibeik M, Kargar H (2007) Appl Catal A Gen 325:99
Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Chahardahcheric S, Tavakoli Z (2008) J Organomet Chem 693:2041
Lee ASY, Hu YJ, Chu SF (2001) Tetrahedron 57:2121
Marcune FB, Karady S, Dolling UH, Novak JT (1999) J Org Chem 64:2446
Ronald RC, Winkle MR (1983) Tetrahedron 39:2031
Acknowledgments
We are thankful to the Center of Excellence of Chemistry of University of Isfahan (CECUI) for financial support of this work.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Moghadam, M., Tangestaninejad, S., Mirkhani, V. et al. Highly efficient and selective methoxymethylation of alcohols and phenols catalyzed by reusable ZrO(OTf)2 under solvent-free conditions. Monatsh Chem 141, 641–647 (2010). https://doi.org/10.1007/s00706-010-0310-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-010-0310-8