European Journal of Chemistry

Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals



Main Article Content

Chandrakala Ummadisetti
Badari Narayana Prasad Rachapudi
Lakshmi Anu Prabhavathi Devi Bethala

Abstract

Glycerol-based SO3H-functionalized carbon catalyst was demonstrated as an efficient and recyclable green catalyst for the chemoselective synthesis of pentaerythritol diacetals with aromatic aldehydes in the presence of ketones in excellent yields in toluene at 80 °C. In addition, the catalyst also has the capability for the deprotection of pentaerythritol diacetals in methanol at reflux temperature. The recovered catalyst without any pre-treatment was reused for 5 cycles without any deactivation and leaching into the reaction medium under optimum conditions.


icon graph This Abstract was viewed 2691 times | icon graph Article PDF downloaded 1126 times

How to Cite
(1)
Ummadisetti, C.; Rachapudi, B. N. P.; Bethala, L. A. P. D. Glycerol-Based SO3H-Carbon Catalyst: A Green Recyclable Catalyst for the Chemoselective Synthesis of Pentaerythritol Diacetals. Eur. J. Chem. 2014, 5, 536-540.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Taylor, P. Mechanism and Synthesis, Royal Society of Chemistry, Cambridge, UK. 2002, 32.

[2]. Brown, J.; Lenhard, R. H.; Berstein, S. J. Am. Chem. Soc. 1964, 86, 2183-2187.
http://dx.doi.org/10.1021/ja01065a016

[3]. Saniger, E.; Campos, J. M.; Entrena, A.; Marchal, J. A.; Boulaiz, H.; Aranega, A.; Gallo, M. A.; Espinosa, A. Tetrahedron 2003, 59, 8017-8026.
http://dx.doi.org/10.1016/j.tet.2003.08.016

[4]. Bruns, K.; Conrad, J.; Steigel, A. Tetrahedron 1979, 35, 2523-2530.
http://dx.doi.org/10.1016/0040-4020(79)88015-1

[5]. Marrian, S. F. Chem. Rev. 1948, 43, 149-202.
http://dx.doi.org/10.1021/cr60134a004

[6]. Zhang, Z. H.; Li, T. S.; Jin, T. S.; Li, J. T. J. Chem. Res. (S). 1998, 10, 640-641.
http://dx.doi.org/10.1039/a803046d

[7]. Perner, J.; Stork, K.; Merger, F.; Oppenlaender, K. Ger. Offen, 1978, 2707875 (Chem. Abstr. 1978, 89, 181503x).

[8]. Jin, T.; Yang, M.; Wang, X.; Feng, G.; Li, T. J. Chem. Res. 2004, 3, 203-205.
http://dx.doi.org/10.3184/0308234041640654

[9]. Jermy, B. R.; Pandurangan, A. Catal. Comm. 2006, 7, 921-925.
http://dx.doi.org/10.1016/j.catcom.2006.03.021

[10]. Deng, G.; Ren, T. J. Chem. Res. 2003, 1, 24-25.
http://dx.doi.org/10.3184/030823403103172805

[11]. Jin, T. S.; Li, T. S.; Zhang, Z. H. Synth. Commun. 1999, 29, 1601-1606.
http://dx.doi.org/10.1080/00397919908086141

[12]. Jin, T. S.; Ma, Y. R.; Li, T. S. J. Chem. Res. (S). 1999, 268-269.

[13]. Wang, G.; Song, G.; Yang, T.; Yang, L.; Suo, J. J. Mol. Catal A: Chem. 2005, 233, 121-126.
http://dx.doi.org/10.1016/j.molcata.2005.02.006

[14]. Wang, Y.; Xu, Y. N.; Wang, Z. Z.; Dai, L. Y. Chin. Chem. Lett. 2010, 21, 524-528.
http://dx.doi.org/10.1016/j.cclet.2009.12.014

[15]. Jermy, B. R.; Pandurangan, A. J. Mol. Catal A: Chem. 2006, 256, 184-192.
http://dx.doi.org/10.1016/j.molcata.2006.04.045

[16]. Shaterian, H. R.; Rigi, F. Chin. J. Chem. 2012, 30, 695-698.
http://dx.doi.org/10.1002/cjoc.201280002

[17]. Shaterian, H. R.; Azizi, K.; Fahimi, N. Chem. Sci. Trans. 2012, 1(1), 85-90.
http://dx.doi.org/10.7598/cst2012.141

[18]. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayash, S.; Domen, K. Angew. Chem. Int. Ed. 2004, 43, 2955-2958.
http://dx.doi.org/10.1002/anie.200453947

[19]. Toda, M.; Takagaki, A.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Dome, K.; Hara, M. Nature 2005, 438, 178-178.
http://dx.doi.org/10.1038/438178a

[20]. Takagaki, A.; Toda, M.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Catal. Today 2006, 116, 157-161.
http://dx.doi.org/10.1016/j.cattod.2006.01.037

[21]. Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wu, H. Green Chem. 2007, 9, 434-437.
http://dx.doi.org/10.1039/b615447f

[22]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Prasad, P. S. S.; Jagannadh, B.; R. B. N. Prasad, Chem. Sus. Chem. 2009, 2, 617-620.
http://dx.doi.org/10.1002/cssc.200900097

[23]. Prabhavaeti Devi, B. L. A.; Gangadhar, K. N.; Kumar, K. L. N. S.; Sanker, K. S.; Prasad, R. B. N.; Prasad, P. S. S. J. Mol. Cat. A: Chem. 2011, 345, 96-100.
http://dx.doi.org/10.1016/j.molcata.2011.05.025

[24]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhsmi, K.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1126-1129.
http://dx.doi.org/10.1016/j.tetlet.2011.12.092

[25]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1968-1973.
http://dx.doi.org/10.1016/j.tetlet.2012.02.018

[26]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Vijay, M.; Prabhavaeti Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 2636-2638.
http://dx.doi.org/10.1016/j.tetlet.2012.03.051

[27]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Chandrakala, U.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497-3501.
http://dx.doi.org/10.1016/j.tetlet.2012.04.122

[28]. Rao, B. M.; Reddy, G. N.; Reddy, T. V. K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N.; Yadav, J. S.; Reddy, B. V. S.; Tetrahedron Lett. 2013, 54, 2466-2471.
http://dx.doi.org/10.1016/j.tetlet.2013.02.089

[29]. Gangadhar, K. N.; Vijay, M.; Prasad, R. B. N.; Prabhavathi Devi, B. L. A. Green Sust. Chem. 2013, 3, 122-218.

[30]. Manneganti, V.; Rachapudi, B. N. P.; Bethala, L. A. P. D. Eur. J. Chem. 2014, 5(1), 167-170.
http://dx.doi.org/10.5155/eurjchem.5.1.167-170.917

Supporting Agencies

Department of Science and Technology (DST), Government of India, New Delhi, India
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).