

Decatungstodivanadogermanic heteropoly acid (H6GeW10V2O40.22H2O): A novel, green and reusable catalyst for efficient acetylation of alcohols and phenols under solvent-free conditions
Saeid Farhadi (1,*)


(1) Department of Chemistry, Faculty of Science, Lorestan University, Khoramabad, IR-68135-465, Iran
(2) Department of Chemistry, Faculty of Science, Lorestan University, Khoramabad, IR-68135-465, Iran
(*) Corresponding Author
Received: 04 Jul 2010 | Accepted: 01 Sep 2010 | Published: 22 Dec 2010 | Issue Date: December 2010
Abstract
Decatungstodivanadogermanic acid (H6GeW10V2O40.22H2O) was used as a novel and green heterogeneous catalyst for the acetylation of hydroxy compounds under solvent-free conditions at room temperature. Efficient and selective acetylation of various alcohols and phenols was conducted with acetic anhydride as an acetylating agent over H6GeW10V2O40.22H2O under solvent-free conditions. All acetylated products were selectively obtained in excellent yields with very short reaction times. The reaction times were longer for the acetylation of phenols than for alcohols, so that an alcoholic OH group could be selectively acetylated in the presence of a phenolic OH group by the appropriate choice of reaction time. The catalyst can be recycled several times without observable loss of activity and selectivity.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF

DOI: 10.5155/eurjchem.1.4.335-340.194
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Citations
[1]. Alina Marieta Simion, Iwao Hashimoto, Yoshiharu Mitoma, Naoyoshi Egashira, Cristian Simion
O-Acylation of Substituted Phenols with Various Alkanoyl Chlorides Under Phase-Transfer Catalyst Conditions
Synthetic Communications 42(6), 921, 2012
DOI: 10.1080/00397911.2011.584007

[2]. Gavin W. Stewart, Peter E. Maligres, Carl A. Baxter, Ellyn M. Junker, Shane W. Krska, Jeremy P. Scott
An approach to heterodiarylmethanes via sp2–sp3 Suzuki−Miyaura cross-coupling
Tetrahedron 72(26), 3701, 2016
DOI: 10.1016/j.tet.2016.02.030

[3]. Fatemeh Tamaddon, Davood Azadi
Synthesis and identification of nicotinium sulfate (3-(1-methylpyrrolidin-2-yl)pyridine:H 2 SO 4 ) from tobacco-extracted nicotine: A protic ionic liquid and biocompatible catalyst for selective acetylation of amines
Journal of Molecular Liquids 255, 406, 2018
DOI: 10.1016/j.molliq.2017.12.107

[4]. Srinivasa Rao Jetti, Divya Verma, Shubha Jain
Microwave-Assisted Synthesis of Spirofused Heterocycles Using Decatungstodivanadogermanic Heteropoly Acid as a Novel and Reusable Heterogeneous Catalyst under Solvent-Free Conditions
Journal of Catalysts 2013, 1, 2013
DOI: 10.1155/2013/392162

[5]. Manjulla Gupta, Monika Gupta
Doping of copper (I) oxide onto a solid support as a recyclable catalyst for acetylation of amines/alcohols/phenols and synthesis of trisubstituted imidazole
Journal of the Iranian Chemical Society 13(2), 231, 2016
DOI: 10.1007/s13738-015-0730-9

References
[1]. Wuts, M.; Greene, T. W. Green’s Protective Groups in Organic Synthesis, 4th edition, John Wiley & Sons, 2007, pp. 222-298.
[2]. Hanson, J. R. Protecting Groups in Organic Synthesis, first edition, Blackwell Science, 1999.
[3]. Vedejs, E.; Diver, S. T. J. Am. Chem. Soc. 1993, 115, 3358–3359.
doi:10.1021/ja00061a056
[4]. Iqbal, J.; Srivastava, R. R. J. Org. Chem. 1992, 57, 2001–2007
doi:10.1021/jo00033a020
[5]. Backer, R. H.; Bordwell, F. G. Org. Synth. 1995, 3, 141–142.
[6]. Chandrasekhar, S.; Ramachander, T.; Takhi, M. Tetrahedron Lett. 1998, 39, 3263–3266.
doi:10.1016/S0040-4039(98)00465-1
[7]. Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 6749–6753.
doi:10.1016/S0040-4039(03)01641-1
[8]. De, S. K. Tetrahedron Lett. 2004, 45, 2919–2922.
doi:10.1016/j.tetlet.2004.02.071
[9]. Miyashita, M.; Shiina, I.; Miyoshi, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1993, 66, 1516–1520.
doi:10.1246/bcsj.66.1516
[10]. Nakae, Y.; Kusaki, I.; Sato, T. Synlett 2001, 10, 1584–1586.
doi:10.1055/s-2001-17483
[11]. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Sambri, L. Synlett 2003, 39–42.
[12]. Bartoli, G.; Bosco, M.; Dalpozzo, R.; Marcantoni, E.; Massaccesi, M.; Sambri, L. Eur. J. Org. Chem. 2003, 4611–4617.
doi:10.1002/ejoc.200300458
[13]. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560–4567.
doi:10.1021/jo952237x
PMid:11667380
[14]. Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265–266.
doi:10.1055/s-1996-5376
[15]. Procopiou, P. A.; Baugh, S. P. D.; Flack, S. S.; Inglis, G. G. A. J. Org. Chem. 1998, 63, 2342–2347.
doi:10.1021/jo980011z
[16]. Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett 1999, 11, 1743–1744.
doi:10.1055/s-1999-2941
[17]. Chandra, K. L.; Saravanan, P.; Singh, R. K.; Singh, V. K. Tetrahedron 2002, 58, 1369–1374.
doi:10.1016/S0040-4020(01)01229-7
[18]. Dalpozzo, R.; Nino, A. D.; Maiuolo, L.; Procopio, A.; Nardi, M.; Bartoli, G.; Romeo, R. Tetrahedron Lett. 2003, 44, 5621–5624.
doi:10.1016/S0040-4039(03)01358-3
[19]. Orita, A.; Tanahashi, C.; Kakuda, A.; Otera, J. Angew. Chem., Int. Ed. 2000, 39, 2877–2879.
doi:10.1002/1521-3773(20000818)39:16<2877::AID-ANIE2877>3.0.CO;2-V
[20]. Phukan, P. Tetrahedron Lett. 2004, 45, 4785–4787.
doi:10.1016/j.tetlet.2004.04.076
[21]. Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199–250.
doi:10.1021/cr0200769
PMid:14719975
[22]. Kumar, P.; Pandey, R. K.; Bodas, M. S.; Dongare, M. K. Synlett. 2001, 2, 206–209.
[23]. Sarvari, M. H.; Sharghi, H. Tetrahedron 2005, 61, 10903–10907
doi:10.1016/j.tet.2005.09.002
[24]. Thakuria, H. T.; Borah, B. M.; Das, G. J. Mol. Catal. A: Chem. 2007, 274, 1–10.
doi:10.1016/j.molcata.2007.04.024
[25]. Kantam, M. L.; Ranganath, K. V. S.; Sateesh, M.; Sreedhar, B.; Choudary, B. M. J. Mol. Catal. A: Chem. 2006, 244, 213–216.
doi:10.1016/j.molcata.2005.09.004
[26]. Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 15, 1896–1897.
doi:10.1039/b304178f
PMid:12932021
[27]. Shirini, F.; Zolfigol, M. A.; Mohammadi, K. Bull. Korean Chem. Soc. 2004, 25, 325–327.
doi:10.5012/bkcs.2004.25.2.325
[28]. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.; Amani, K. Chem. Commun. 2003, 764–765.
doi:10.1039/b300775h
PMid:12703812
[29]. Chavan, S. P.; Anand, R.; Pasupathy, K.; Rao, B. S. Green Chem. 2001, 3, 320–322.
doi:10.1039/b109093c
[30]. Kumareswaran, R.; Pachamuthu, K.; Vankar, Y.D. Synlett 2000, 11, 1652–1654.
[31]. Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003, 44, 3521–3525.
doi:10.1016/S0040-4039(03)00683-X
[32]. Ghosh, R.; Maiti, S.; Chakraborty, A. Tetrahedron Lett. 2005, 46, 147–151.
doi:10.1016/j.tetlet.2004.10.164
[33]. Joseph, J. K.; Jain, S. L.; Sain, B. J. Mol. Catal. A: Chem. 2007, 267, 108–111.
doi:10.1016/j.molcata.2006.11.026
[34]. Das, B.; Thirupathi, P. J. Mol. Catal. A: Chem. 2007, 269, 12–16.
doi:10.1016/j.molcata.2006.12.029
[35]. Ratnam, K. J.; Reddy, R. S.; Sekhar, N. S.; Kantam, M. L.; Figueras, F. J. Mol. Catal. A: Chem. 2007, 276, 230–234.
doi:10.1016/j.molcata.2007.07.008
[36]. Satam, J. R.; Jayaram, R.V. Catal. Commun. 2008, 9, 2365–2370.
doi:10.1016/j.catcom.2008.05.033
[37]. Wang, W.; Cheng, W.; Shao, L.; Yang, J. Catal. Lett. 2008, 121, 77–80.
doi:10.1007/s10562-007-9295-2
[38]. Rajabi, F. Tetrahedron Lett. 2009, 50, 395–397.
doi:10.1016/j.tetlet.2008.11.024
[39]. Niknam, K.; Saberi, D. Tetrahedron Lett. 2009, 50, 5210–5214.
doi:10.1016/j.tetlet.2009.06.140
[40]. Niknam, K.; Saberi, D. Appl. Catal. A: Gen. 2009, 366, 220–225.
doi:10.1016/j.apcata.2009.07.014
[41]. Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171–198.
doi:10.1021/cr960400y
PMid:11851502
[42]. Kozhevnikov, I. V. J. Mol. Catal. A: Chem. 2007, 262, 86–92.
doi:10.1016/j.molcata.2006.08.072
[43]. Izumi, Y.; Urabe, K.; Onaka, M. Zeolite, Clay and Heteropoly Acid in Organic Reactions, Kodansha-VCH, 1992.
[44]. Farhadi, S.; Taherimehr, M. Catal. Commun. 2008, 9, 703–708.
doi:10.1016/j.catcom.2007.08.006
[45]. Farhadi, S.; Taherimehr, M. Acta Chim. Slov. 2008, 55, 637–643.
[46]. Farhadi, S.; Zaidi. M. J. Mol. Catal. A: Chem. 2009, 299, 18–25.
doi:10.1016/j.molcata.2008.10.013
[47]. Wu, Q.; Chen, Q.; Cai, X.; Wang, J.; Zhang, J. Mater. Lett. 2007, 61, 663–665.
doi:10.1016/j.matlet.2006.05.030
[48]. Sang, X. G.; Wu, Q. Y. Chem. Lett. 2004, 33, 1518–1519.
doi:10.1246/cl.2004.1518
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.1.4.335-340.194

















European Journal of Chemistry 2010, 1(4), 335-340 | doi: https://doi.org/10.5155/eurjchem.1.4.335-340.194 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.