Yttrium Nitrate mediated Nitration
NMR data.14 Further study of this method revealed that
aromatic ring without phenolic −OH is not reactive
(entry 7–10, Table 2). Presence of electron withdrawing
group makes the process slow. Surprisingly, activated
ring containing acetanilide and aniline (entry 9 and
10, Table 2) did not react under the described method.
This suggests that the nitration reaction is selective to
phenols.
promoted rapid nitration of phenolic compounds with
calcium nitrate Tetrahedron Lett. 47 1885
3. Jacoway J, Kumar G G K S N and Laali K K 2012
Aromatic nitration with bismuth nitrate in ionic liq-
uids and in molecular solvents: A comparative study of
Bi(NO3)3·5H2O/[bmim][PF6] and Bi(NO3)3·5H2O/1,2-
DCE systems Tetrahedron Lett. 53 6782
4. Chen L-Y, Liu T, Zhou X and Sun Z 2014 A practical
approach for regioselective mono-nitration of phenols
under mild conditions ARKIVOC (v) 64
5. Ali M, Zolfigol E G and Madrakian E 2001 Nitration
Of Phenols Under Mild and Heterogeneous Conditions
Molecules 6 614
6. Hosseini-Sarvari M, Tavakolian M and Ashenagar 2010
Nitration of aromatic compounds using alumina sulfu-
ric acid (ASA) as a novel heterogeneous system and Mg
(NO3)2.6H2O as nitrating agent in water Iran. J. Sci.
Technol., Transaction A 34 215
7. Nowrouzi N and Zareh Jonaghani M 2011 Nitration of
aromatic compounds under neutral conditions using the
Ph2PCl/I2/AgNO3 reagent system Tetrahedron Lett. 52
5081
8. Selvam J J P, Suresh V, Rajesh K, Reddy S R and
Venkateswarlu Y 2006 Highly efficient nitration of phe-
nolic compounds by zirconyl nitrate Tetrahedron Lett.
47 2507
9. Gu S, Jing H, Wu J and Liang Y 1997 A Convenient
Method of Meta-Directing Nitration of 3-Substituted
Phenol by Lanthanide (III) Nitrates Synth. Commun. 27
2793
10. Politi L, Vignali C and Polettini A 2007 LC-MS-MS
Analysis of 2,4-Dinitrophenol and Its Phase I and II
Metabolites in a Case of Fatal Poisoning J. Anal. Toxi-
col. 31 55
4. Conclusions
In summary, Y(NO3)3.6H2O in acetic acid was found to
be an efficient nitrating reagent for the synthesis of nitro
substituted phenolics at room temperature. The method
offers several advantages including rapid nitration, high
yield, simple experimental condition, and easy product
isolation procedure. The method is selective for nitra-
tion of phenols and offers a suitable alternative for syn-
thesizing nitrophenols. Y(NO3)3.6H2O in acetic acid
gave different selectivity as compared to the previously
reported nitration in ethylacetate under refluxing con-
dition. Detailed mechanistic investigation as well as
further scope of the nitration is under investigation.
Supplementary Information (SI)
Experimental details and NMR and LC-MS spectral data for
Acknowledgements
11. Perez R A, Fernandez-Alvarez E, Nieto O and Piedrafita
F J 1992 Dihydroxynitrobenzaldehydes and hydrox-
ymethoxynitrobenzaldehydes: Synthesis and biological
activity as catechol-O-methyltransferase inhibitors J.
Med. Chem. 35 4584
12. Fitzgerald L J and Gerkin R E 1998 Phenolphthalein and
3’,3"-Dinitrophenolphthalein Acta Cryst. C54 535
13. van Kampen E J 1953 Synthesis of potential chemother-
apeutics in bile duct infections (II) Recueil des Travaux
Chimiques des Pays-Bas 72 995
Financial support from the Department of Science and Tech-
nology (SERB), New Delhi (EMR/2014/000542), is grate-
fully acknowledged. Special thanks to Head, Department
of chemistry, North Bengal University for providing NMR
facility.
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