European Journal of Chemistry

Selective iodination of 2-acetyl-1-naphthol using iodine and iodic acid under solvent-free grinding technique



Main Article Content

Sainath Zangade
Shyam Mokle
Avinash Shinde
Yeshwant Vibhute

Abstract

Selective electrophilic iodination of 2-acetyl-1-naphthol was achieved using iodine and iodic acid in combination with grinding at room temperature under solvent-free conditions to yield 1-(1-hydroxy-4-iodo-naphthalen-2-yl)-ethanone. Grinding mode of reactions has not only of interest from economical point of view, in many cases they also offer considerable advantages in terms of yield, mild reaction  conditions, selectivity and simplicity of reaction procedure.

3_3_314_315_800


icon graph This Abstract was viewed 1888 times | icon graph Article PDF downloaded 677 times

How to Cite
(1)
Zangade, S.; Mokle, S.; Shinde, A.; Vibhute, Y. Selective Iodination of 2-Acetyl-1-Naphthol Using Iodine and Iodic Acid under Solvent-Free Grinding Technique. Eur. J. Chem. 2012, 3, 314-315.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Diederich, F.; Stang, P. J. Metal-Catalyzed Cross Coupling Reactions; Wiley-VCH: Weinheim, Germany, 1998.
http://dx.doi.org/10.1002/9783527612222

[2]. Seevers, R. H.; Counsell, R. Chem. Rev. 1982, 82, 575-590.
http://dx.doi.org/10.1021/cr00052a002

[3]. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2002, 102, 4009-4092.
http://dx.doi.org/10.1021/cr0102967
PMid:12428984

[4]. Olivera, R.; San Martin, R.; Dominguez, E. Tetrahedron Lett. 2000, 41, 4357-4360.
http://dx.doi.org/10.1016/S0040-4039(00)00622-5

[5]. Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225-6228.
http://dx.doi.org/10.1016/S0040-4039(97)01431-7

[6]. Zupan, M.; Iskra, J.; Stavber, S. Tetahedron Lett. 1997, 38, 6305-6306.
http://dx.doi.org/10.1016/S0040-4039(97)01414-7

[7]. Carreno, M. C.; Ruano, J. G.; Sanz, G.; Toledo, M. A.; Urbano, A. Tetrahedron Lett. 1996, 37, 4081-4084.
http://dx.doi.org/10.1016/0040-4039(96)00738-1

[8]. Akhlaghinia, B.; Rahmani, M. J. Turk. Chem. 2009, 33, 67-72.

[9]. Orito, K.; Hatakeyama, T.; Takeo, M. Synthesis 1995, 1273-1277.
http://dx.doi.org/10.1055/s-1995-4089

[10]. Hubig, S. M.; Jung, W.; Kochi, J. K. J. Org. Chem. 1994, 59, 6233-6244.
http://dx.doi.org/10.1021/jo00100a025

[11]. Barluenga, J.; Gonzalez, J. M.; Garcia-Martin, M. A.; Campos, P. J.; Asensia, G. J. Org. Chem. 1993, 58, 2058-2060.
http://dx.doi.org/10.1021/jo00060a020

[12]. Olah, G. A.; Wang, D.; Sandford, G.; Prakash, G. K. S. J. Org. Chem. 1993, 58, 3194-3195.
http://dx.doi.org/10.1021/jo00063a052

[13]. Sy, W. W. Tetrahedron Lett. 1993, 34, 6223-6224.
http://dx.doi.org/10.1016/S0040-4039(00)73715-4

[14]. Bachki, A.; Foubelo, F.; Yus, M. Tetrahedron 1994, 50, 5139-5146.
http://dx.doi.org/10.1016/S0040-4020(01)90424-7

[15]. Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287-5291.
http://dx.doi.org/10.1021/jo00305a026

[16]. Zangade, S.; Mokle, S.; Chavan, S.; Vibhute, Y. Orbital Elec. J. Chem. 2011, 3, 144-149.

[17]. Zangade, S.; Shinde, A.; Patil, A.; Vibhute, Y. Eur. J. Chem. 2012, 3, 208-210.
http://dx.doi.org/10.5155/eurjchem.3.2.208-210.581

[18]. Zangade, S.; Shinde, A.; Vibhute, A.; Vibhute, Y. Pak. J. Chem. 2012, 2, 18-23.

[19]. Shinde, A. T.; Zangade, S. B.; Chavan, S. B.; Vibhute, A. Y.; Nalwar, Y. S.; Vibhute, Y. B. Synth. Commun. 2010, 40, 3506-3513.
http://dx.doi.org/10.1080/00397910903457332

[20]. Bose, A. K.; Pednekar, S.; Ganguly, S. N.; Chakraborty, G.; Manhas, M. S. Tetrahedron Lett. 2004, 45, 8351-8353.
http://dx.doi.org/10.1016/j.tetlet.2004.09.064

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).