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Efficient Synthesis of a-Hydroxyacetophenone via Microwave Irradiation of a-Bromoacetophenone from Acetophenone
Corresponding Author(s) : Xinhua Peng
Asian Journal of Chemistry,
Vol. 27 No. 9 (2015): Vol 27 Issue 9
Abstract
Herein, we reported a new and efficient approach starting from acetophenone. In this work, a-hydroxyacetophenone was prepared under microwave irradiation of a-bromoacetophenone which was efficiently prepared by the use of HBr/H2O2 system.
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- A. Podgoršek, S. Stavber, M. Zupan and J. Iskra, Tetrahedron Lett., 65, 4429 (2009); doi:10.1016/j.tet.2009.03.034.
- C.J. Li and T.H. Chan, Tetrahedron Lett., 55, 11149 (1999); doi:10.1016/S0040-4020(99)00641-9.
- K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi and T. Horaguchi, Chem. Commun., 470 (2004); doi:10.1039/B315340A.
- B. Das, K. Venkateswarlu, G. Mahender and I. Mahender, Tetrahedron Lett., 46, 3041 (2005); doi:10.1016/j.tetlet.2005.03.020.
- D. Yang, Y.-L. Yan and B. Lui, Org. Chem., 67, 7429 (2002); doi:10.1021/jo026025t.
- I.E. Baciocch, I.M. Biett and M.F. Gerini, L. Manduchi, M. Salamone and S. Steenken, Chemistry, 9, 153 (2001).
- T. Cuvigny, G. Valette, M. Larcheveque and H.J. Normant, Org. Chem., 155, 147 (1978); doi:10.1016/S0022-328X(00)93286-8.
- R.M. Moriarty, H. Hu and S.C. Gupta, Tetrahedron Lett., 22, 1283 (1981); doi:10.1016/S0040-4039(01)90297-7.
- Y. Horiguchi, E. Nakamura and I. Kuwajima, Tetrahedron Lett., 30, 3323 (1989); doi:10.1016/S0040-4039(00)99233-5.
- C.A. Horiuchi, A. Takeda, W. Chai, K. Ohwada, S.J. Ji and T.T. Takahashi, Tetrahedron Lett., 44, 9307 (2003); doi:10.1016/j.tetlet.2003.10.082.
- W. Chai, A. Takeda, M. Hara, S.-J. Ji and C.A. Horiuchi, Tetrahedron Lett., 61, 2453 (2005); doi:10.1016/j.tet.2005.01.010.
- X. Beebe, A.M. Nilius, P.J. Merta, N.B. Soni, M.H. Bui, R. Wagner and B.A. Beutel, Chem. Lett., 13, 3133 (2003); doi:10.1016/S0960-894X(03)00727-3.
- S. Navath, Synlett, 1267 (2008); doi:10.1055/s-2008-1066999.
- T. Utsukihara, H. Nakamura, M. Watanabe and C.A. Horiuchi, Tetrahedron Lett., 47, 9359 (2006); doi:10.1016/j.tetlet.2006.10.087.
- A. Podgoršek, M. Zupan and J. Iskra, Angew. Chem., 48, 8424 (2009); doi:10.1002/anie.200901223.
- K. Bougrin, A. Loupy and M.J. Soufiaoui, Photochem. Photobiol. C, 6, 139 (2005); doi:10.1016/j.jphotochemrev.2005.07.001.
- G.W. Kabalka, L. Wang, V. Namboodiri and R.M. Pagni, Tetrahedron Lett., 41, 5151 (2000); doi:10.1016/S0040-4039(00)00774-7.
- R.K. Arvela, N.E. Leadbeater, T.L. Mack and C.M. Kormos, Tetrahedron Lett., 47, 217 (2006); doi:10.1016/j.tetlet.2005.10.153.
- R.K. Arvela and N.E.J. Leadbeater, Org. Chem., 70, 1786 (2005); doi:10.1021/jo048052k.
References
A. Podgoršek, S. Stavber, M. Zupan and J. Iskra, Tetrahedron Lett., 65, 4429 (2009); doi:10.1016/j.tet.2009.03.034.
C.J. Li and T.H. Chan, Tetrahedron Lett., 55, 11149 (1999); doi:10.1016/S0040-4020(99)00641-9.
K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi and T. Horaguchi, Chem. Commun., 470 (2004); doi:10.1039/B315340A.
B. Das, K. Venkateswarlu, G. Mahender and I. Mahender, Tetrahedron Lett., 46, 3041 (2005); doi:10.1016/j.tetlet.2005.03.020.
D. Yang, Y.-L. Yan and B. Lui, Org. Chem., 67, 7429 (2002); doi:10.1021/jo026025t.
I.E. Baciocch, I.M. Biett and M.F. Gerini, L. Manduchi, M. Salamone and S. Steenken, Chemistry, 9, 153 (2001).
T. Cuvigny, G. Valette, M. Larcheveque and H.J. Normant, Org. Chem., 155, 147 (1978); doi:10.1016/S0022-328X(00)93286-8.
R.M. Moriarty, H. Hu and S.C. Gupta, Tetrahedron Lett., 22, 1283 (1981); doi:10.1016/S0040-4039(01)90297-7.
Y. Horiguchi, E. Nakamura and I. Kuwajima, Tetrahedron Lett., 30, 3323 (1989); doi:10.1016/S0040-4039(00)99233-5.
C.A. Horiuchi, A. Takeda, W. Chai, K. Ohwada, S.J. Ji and T.T. Takahashi, Tetrahedron Lett., 44, 9307 (2003); doi:10.1016/j.tetlet.2003.10.082.
W. Chai, A. Takeda, M. Hara, S.-J. Ji and C.A. Horiuchi, Tetrahedron Lett., 61, 2453 (2005); doi:10.1016/j.tet.2005.01.010.
X. Beebe, A.M. Nilius, P.J. Merta, N.B. Soni, M.H. Bui, R. Wagner and B.A. Beutel, Chem. Lett., 13, 3133 (2003); doi:10.1016/S0960-894X(03)00727-3.
S. Navath, Synlett, 1267 (2008); doi:10.1055/s-2008-1066999.
T. Utsukihara, H. Nakamura, M. Watanabe and C.A. Horiuchi, Tetrahedron Lett., 47, 9359 (2006); doi:10.1016/j.tetlet.2006.10.087.
A. Podgoršek, M. Zupan and J. Iskra, Angew. Chem., 48, 8424 (2009); doi:10.1002/anie.200901223.
K. Bougrin, A. Loupy and M.J. Soufiaoui, Photochem. Photobiol. C, 6, 139 (2005); doi:10.1016/j.jphotochemrev.2005.07.001.
G.W. Kabalka, L. Wang, V. Namboodiri and R.M. Pagni, Tetrahedron Lett., 41, 5151 (2000); doi:10.1016/S0040-4039(00)00774-7.
R.K. Arvela, N.E. Leadbeater, T.L. Mack and C.M. Kormos, Tetrahedron Lett., 47, 217 (2006); doi:10.1016/j.tetlet.2005.10.153.
R.K. Arvela and N.E.J. Leadbeater, Org. Chem., 70, 1786 (2005); doi:10.1021/jo048052k.