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Nitration of Methyl Eugenol Derived from Clove Oil
Corresponding Author(s) : I.M. Sudarma
Asian Journal of Chemistry,
Vol. 32 No. 1 (2020): Vol 32 Issue 1
Abstract
No report is available in literature for the nitration of methyl eugenol. The main goal of this work is to find an efficient method for the synthesis of 5-nitro-methyl eugenol. 5-Nitro-methyl eugenol is of considerable importance in the production of other fine chemicals such as 5-amino-methyl eugenol for further chemical synthesis and has also possible to enhance its biological properties and other applications. The methyl eugenol can be prepared from methylation of eugenol which can be isolated from clove oil. In an attempt to synthesize nitro-methyl eugenol in high yield, three different nitration methods of methyl eugenol have been applied. Method (a) gave 5.97 %, (b) 84.37 % and (c) 11.40 %. Method (b) using a nitrating consisting mixture of HNO3 and H2SO4 under mild condition has been found to give 5-nitro-methyl eugenol in good yield.
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- K.H. Tan and R. Nishida, J. Insect Sci., 12, 1 (2012); https://doi.org/10.1673/031.012.5601.
- P. Sudhakar, P. Latha, Y. Sreenivasulu, B.V. Reddy, T. M. Hemalatha, M. Balakrishna and K.R. Reddy, Indian J. Exp. Biol., 47, 63 (2009).
- P.G. Rossi, L. Bao, A. Luciani, J. Panighi, J.M. Desjobert, J. Costa, J. Casanova, J.M. Bolla and L. Berti, J. Agric. Food Chem., 55, 7332 (2007); https://doi.org/10.1021/jf070674u.
- I.K. Park, J. Kim, S.G. Lee and S.C. Shin, J. Nematol., 39, 275 (2007);
- Y.K. Choi, G.S. Cho, S. Hwang, B.W. Kim, J.H. Lim, J.C. Lee, H.C. Kim , W.K. Kim and Y.S. Kim, Free Radic. Res., 44, 925 (2010); https://doi.org/10.3109/10715762.2010.490837.
- L. Yin, Z. Sun, Q. Ren, X. Su and D. Zhang, J. BUON, 23, 1174 (2018).
- R.L. Smith, T.B. Adams, J. Doull, V.J. Feron, J.I. Goodman, L.J. Marnett, P.S. Portoghese, W.J. Waddell, B.M. Wagner, A.E. Rogers, J. Caldwell and I.G. Sipes, Food Chem. Toxicol., 40, 851 (2002); https://doi.org/10.1016/S0278-6915(02)00012-1.
- I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian J. Chem., 26, 173 (2014).
- M.A. Zolfigol, E. Ghaemi and E. Madrakian, Molecules, 6, 614 (2001); https://doi.org/10.3390/60700614.
- R.O.C. Norman and R. Taylor, Electrophilic Substitution in Benzenoid Compounds, Elsevier: Amsterdan, p. 301 (1965).
- G. Booth, Nitro Compounds, Aromatic, Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, edn 6 (2007).
- C. Waterlot, B. Haskiak and D. Couturier, J. Chem. Res., 106 (2000); https://doi.org/10.3184/030823400103166788.
- Riyanto, H. Sastrohamidjojo and E. Fariyatun, IOSR J. Appl. Chem., 9, 105 (2016).
- B. Baghernejad, M.M. Heravi, H.A. Oskooie and Y.S. Beheshtiha, Gazi Univ. J. Sci., 22, 169 (2009).
References
K.H. Tan and R. Nishida, J. Insect Sci., 12, 1 (2012); https://doi.org/10.1673/031.012.5601.
P. Sudhakar, P. Latha, Y. Sreenivasulu, B.V. Reddy, T. M. Hemalatha, M. Balakrishna and K.R. Reddy, Indian J. Exp. Biol., 47, 63 (2009).
P.G. Rossi, L. Bao, A. Luciani, J. Panighi, J.M. Desjobert, J. Costa, J. Casanova, J.M. Bolla and L. Berti, J. Agric. Food Chem., 55, 7332 (2007); https://doi.org/10.1021/jf070674u.
I.K. Park, J. Kim, S.G. Lee and S.C. Shin, J. Nematol., 39, 275 (2007);
Y.K. Choi, G.S. Cho, S. Hwang, B.W. Kim, J.H. Lim, J.C. Lee, H.C. Kim , W.K. Kim and Y.S. Kim, Free Radic. Res., 44, 925 (2010); https://doi.org/10.3109/10715762.2010.490837.
L. Yin, Z. Sun, Q. Ren, X. Su and D. Zhang, J. BUON, 23, 1174 (2018).
R.L. Smith, T.B. Adams, J. Doull, V.J. Feron, J.I. Goodman, L.J. Marnett, P.S. Portoghese, W.J. Waddell, B.M. Wagner, A.E. Rogers, J. Caldwell and I.G. Sipes, Food Chem. Toxicol., 40, 851 (2002); https://doi.org/10.1016/S0278-6915(02)00012-1.
I.M. Sudarma, N. Wazni, N. Wildawaty, E. Yuanita and I.W. Suana, Asian J. Chem., 26, 173 (2014).
M.A. Zolfigol, E. Ghaemi and E. Madrakian, Molecules, 6, 614 (2001); https://doi.org/10.3390/60700614.
R.O.C. Norman and R. Taylor, Electrophilic Substitution in Benzenoid Compounds, Elsevier: Amsterdan, p. 301 (1965).
G. Booth, Nitro Compounds, Aromatic, Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, edn 6 (2007).
C. Waterlot, B. Haskiak and D. Couturier, J. Chem. Res., 106 (2000); https://doi.org/10.3184/030823400103166788.
Riyanto, H. Sastrohamidjojo and E. Fariyatun, IOSR J. Appl. Chem., 9, 105 (2016).
B. Baghernejad, M.M. Heravi, H.A. Oskooie and Y.S. Beheshtiha, Gazi Univ. J. Sci., 22, 169 (2009).