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Microwave-Assisted Acetylation of Phenols without Catalyst Under Solvent Free Condition
Corresponding Author(s) : Yu-Quan Zhang
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
Etherification between phenols with acetic anhydride was tested under different conditions. Phenols were efficiently acylated with acetic anhydride to give phenol acetate derivatives in good high yields without catalyst and solventless conditions under microwave irradiation.
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- A.L. Pearson and W.J. Roush, Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups; John Wiley & Sons: UK, pp. 9-16 (1999).
- R.I. Zhdanov and S.M. Zhenodarova, Synthesis, 222 (1975); doi:10.1055/s-1975-23714.
- W. Steglich and G. Hofle, Angew. Chem. Int. Ed. Engl., 8, 981 (1969); doi:10.1002/anie.196909811.
- T. Sano, K. Ohaschi and T. Oriyama, Synthesis, 1141 (1999); doi:10.1055/s-1999-3521.
- E. Vedejs, N.S. Bennett, L.M. Conn, S.T. Diver, M. Gingras, S. Lin, P.A. Oliver and M.J. Peterson, J. Org. Chem., 58, 7286 (1993); doi:10.1021/jo00077a064.
- H. Hagiwara, K. Morohashi, H. Sakai, T. Suzuki and M. Ando, Tetrahedron, 54, 5845 (1998); doi:10.1016/S0040-4020(98)00255-5.
- A.C. Cope and E.C. Herrick, Org. Synth., 4, 304 (1963).
- R.H. Baker and F.G. Bordwell, Org. Synth., 3, 141 (1955).
- R. Borah, N. Deka and J.C. Sarma, J. Chem. Res. Synop., 110 (1997); doi:10.1039/a605061a.
- T.S. Jin, J.R. Ma, Z.H. Zhang and T.S. Li, Synth. Commun., 28, 3173 (1998); doi:10.1080/00397919808004417.
- E. Vedejs and O. Daugulis, J. Org. Chem., 61, 5702 (1996); doi:10.1021/jo9609485.
- J. Iqbal and R.R. Srivastava, J. Org. Chem., 57, 2001 (1992); doi:10.1021/jo00033a020.
- S. Chandrasekhar, T. Ramachander and M. Takhi, Tetrahedron Lett., 39, 3263 (1998); doi:10.1016/S0040-4039(98)00465-1.
- T. Okano, K. Miyamoto and K. Kiji, Chem. Lett., 24, 246 (1995); doi:10.1246/cl.1995.246.
- G.W. Breton, J. Org. Chem., 62, 8952 (1997); doi:10.1021/jo971367y.
- A.X. Li, T.S. Li and T.H. Ding, Chem. Commun., 1389 (1997); doi:10.1039/a703389c.
- S.S. Rana, J.J. Barlow and K.L. Matta, Tetrahedron Lett., 22, 5007 (1981); doi:10.1016/S0040-4039(01)92405-0.
- P. Kumar, R.K. Pandey, M.S. Bodas and S.P. Dagade, J. Mol. Catal. Chem., 181, 207 (2002); doi:10.1016/S1381-1169(01)00365-X.
- P. Paul, P. Nanda, R. Gupta and A. Loupy, Tetrahedron Lett., 43, 4261 (2002); doi:10.1016/S0040-4039(02)00732-3.
- V.K. Yadav, K.G. Babu and M. Mittal, Tetrahedron, 57, 7047 (2001); doi:10.1016/S0040-4020(01)00677-9.
- B.M. Choudary, M.L. Kantam and V. Neeraja, J. Mol. Catal. Chem., 140, 25 (1999); doi:10.1016/S1381-1169(98)00214-3.
- A. Orita, K. Sakamoto, Y. Hamada, A. Mitsutome and J. Otera, Tetrahedron, 55, 2899 (1999); doi:10.1016/S0040-4020(99)00072-1.
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- P. Allevi, P. Ciuffreda, A. Longo and M. Anastasia, Tetrahedron Asymm., 9, 2915 (1998); doi:10.1016/S0957-4166(98)00285-7.
- S. Yamada, T. Sugaki and K. Matsuzaki, J. Org. Chem., 61, 5932 (1996); doi:10.1021/jo9522015.
- P.A. Procopiou, S.P.D. Baugh, S.S. Flack and G.G.A. Inglis, Chem. Commun., 2625 (1996); doi:10.1039/cc9960002625.
- A.G.M. Barrett and D. Christopher Braddock, Chem. Commun., 351 (1997); doi:10.1039/a606484a.
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- K. Ishihara, M. Kubota, H. Kurihara and H. Yamamoto, J. Am. Chem. Soc., 117, 4413 (1995); doi:10.1021/ja00120a030.
- K.K. Chauhan, C.G. Frost, I. Love and D. Waite, Synlett, 1743 (1999); doi:10.1055/s-1999-2941.
- G. Bartoli, M. Bosco, E. Marcantoni, L. Sambri and E. Torregiani, Synlett, 209 (1998); doi:10.1055/s-1998-1601.
- G. Bartoli, G. Cupone, R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, L. Sambri and A. Tagarelli, Tetrahedron Lett., 43, 5945 (2002); doi:10.1016/S0040-4039(02)01254-6.
- K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.
- P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
- J. Hamelin, J.-P. Bazureau, F. Texier-Boullet in ed.: A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, pp. 253-294 (2002).
- (a) Y.-Q. Zhang, J. Chem. Res., 365 (2013); (b) L. Bai, J.-X. Wang and Y.M. Zhang, Green Chem., 5, 615 (2003); doi:10.1039/b305191a.
- N. Deka, A.-M. Mariotte and A.Ã. Boumendjel, Green Chem., 3, 263 (2001); doi:10.1039/b107696p.
- T. Ando, J. Yamawaki, T. Kawate, S. Sumi and T. Hanafusa, Bull. Chem. Soc. Jpn., 55, 2504 (1982); doi:10.1246/bcsj.55.2504.
- T.J. Mason and D. Peters, Practical Sonochemistry, Ellis-Horwood, London (2002).
- M. Aloe, Rend. Accad. Sci. Napoli, 27, 75 (1921).
- F.D. Chattaway, J. Chem. Soc., 2495 (1931); doi:10.1039/JR9310002495.
- J. Buckingham and S.M. Donghy, Dictionary of Organic Compounds, Chapman and Hall, New York, edn. 5 (1982).
References
A.L. Pearson and W.J. Roush, Handbook of Reagents for Organic Synthesis: Activating Agents and Protecting Groups; John Wiley & Sons: UK, pp. 9-16 (1999).
R.I. Zhdanov and S.M. Zhenodarova, Synthesis, 222 (1975); doi:10.1055/s-1975-23714.
W. Steglich and G. Hofle, Angew. Chem. Int. Ed. Engl., 8, 981 (1969); doi:10.1002/anie.196909811.
T. Sano, K. Ohaschi and T. Oriyama, Synthesis, 1141 (1999); doi:10.1055/s-1999-3521.
E. Vedejs, N.S. Bennett, L.M. Conn, S.T. Diver, M. Gingras, S. Lin, P.A. Oliver and M.J. Peterson, J. Org. Chem., 58, 7286 (1993); doi:10.1021/jo00077a064.
H. Hagiwara, K. Morohashi, H. Sakai, T. Suzuki and M. Ando, Tetrahedron, 54, 5845 (1998); doi:10.1016/S0040-4020(98)00255-5.
A.C. Cope and E.C. Herrick, Org. Synth., 4, 304 (1963).
R.H. Baker and F.G. Bordwell, Org. Synth., 3, 141 (1955).
R. Borah, N. Deka and J.C. Sarma, J. Chem. Res. Synop., 110 (1997); doi:10.1039/a605061a.
T.S. Jin, J.R. Ma, Z.H. Zhang and T.S. Li, Synth. Commun., 28, 3173 (1998); doi:10.1080/00397919808004417.
E. Vedejs and O. Daugulis, J. Org. Chem., 61, 5702 (1996); doi:10.1021/jo9609485.
J. Iqbal and R.R. Srivastava, J. Org. Chem., 57, 2001 (1992); doi:10.1021/jo00033a020.
S. Chandrasekhar, T. Ramachander and M. Takhi, Tetrahedron Lett., 39, 3263 (1998); doi:10.1016/S0040-4039(98)00465-1.
T. Okano, K. Miyamoto and K. Kiji, Chem. Lett., 24, 246 (1995); doi:10.1246/cl.1995.246.
G.W. Breton, J. Org. Chem., 62, 8952 (1997); doi:10.1021/jo971367y.
A.X. Li, T.S. Li and T.H. Ding, Chem. Commun., 1389 (1997); doi:10.1039/a703389c.
S.S. Rana, J.J. Barlow and K.L. Matta, Tetrahedron Lett., 22, 5007 (1981); doi:10.1016/S0040-4039(01)92405-0.
P. Kumar, R.K. Pandey, M.S. Bodas and S.P. Dagade, J. Mol. Catal. Chem., 181, 207 (2002); doi:10.1016/S1381-1169(01)00365-X.
P. Paul, P. Nanda, R. Gupta and A. Loupy, Tetrahedron Lett., 43, 4261 (2002); doi:10.1016/S0040-4039(02)00732-3.
V.K. Yadav, K.G. Babu and M. Mittal, Tetrahedron, 57, 7047 (2001); doi:10.1016/S0040-4020(01)00677-9.
B.M. Choudary, M.L. Kantam and V. Neeraja, J. Mol. Catal. Chem., 140, 25 (1999); doi:10.1016/S1381-1169(98)00214-3.
A. Orita, K. Sakamoto, Y. Hamada, A. Mitsutome and J. Otera, Tetrahedron, 55, 2899 (1999); doi:10.1016/S0040-4020(99)00072-1.
R. Ballini, G. Bosica, S. Carloni, L. Ciaralli, R. Maggi and G. Sartori, Tetrahedron Lett., 39, 6049 (1998); doi:10.1016/S0040-4039(98)01244-1.
P. Allevi, P. Ciuffreda, A. Longo and M. Anastasia, Tetrahedron Asymm., 9, 2915 (1998); doi:10.1016/S0957-4166(98)00285-7.
S. Yamada, T. Sugaki and K. Matsuzaki, J. Org. Chem., 61, 5932 (1996); doi:10.1021/jo9522015.
P.A. Procopiou, S.P.D. Baugh, S.S. Flack and G.G.A. Inglis, Chem. Commun., 2625 (1996); doi:10.1039/cc9960002625.
A.G.M. Barrett and D. Christopher Braddock, Chem. Commun., 351 (1997); doi:10.1039/a606484a.
K.L. Chandra, P. Saravanan, R.K. Singh and V.K. Singh, Tetrahedron, 58, 1369 (2002); doi:10.1016/S0040-4020(01)01229-7.
K. Ishihara, M. Kubota, H. Kurihara and H. Yamamoto, J. Am. Chem. Soc., 117, 4413 (1995); doi:10.1021/ja00120a030.
K.K. Chauhan, C.G. Frost, I. Love and D. Waite, Synlett, 1743 (1999); doi:10.1055/s-1999-2941.
G. Bartoli, M. Bosco, E. Marcantoni, L. Sambri and E. Torregiani, Synlett, 209 (1998); doi:10.1055/s-1998-1601.
G. Bartoli, G. Cupone, R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, L. Sambri and A. Tagarelli, Tetrahedron Lett., 43, 5945 (2002); doi:10.1016/S0040-4039(02)01254-6.
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000); doi:10.1021/cr940089p.
P. Lidström, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 57, 9225 (2001); doi:10.1016/S0040-4020(01)00906-1.
J. Hamelin, J.-P. Bazureau, F. Texier-Boullet in ed.: A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, pp. 253-294 (2002).
(a) Y.-Q. Zhang, J. Chem. Res., 365 (2013); (b) L. Bai, J.-X. Wang and Y.M. Zhang, Green Chem., 5, 615 (2003); doi:10.1039/b305191a.
N. Deka, A.-M. Mariotte and A.Ã. Boumendjel, Green Chem., 3, 263 (2001); doi:10.1039/b107696p.
T. Ando, J. Yamawaki, T. Kawate, S. Sumi and T. Hanafusa, Bull. Chem. Soc. Jpn., 55, 2504 (1982); doi:10.1246/bcsj.55.2504.
T.J. Mason and D. Peters, Practical Sonochemistry, Ellis-Horwood, London (2002).
M. Aloe, Rend. Accad. Sci. Napoli, 27, 75 (1921).
F.D. Chattaway, J. Chem. Soc., 2495 (1931); doi:10.1039/JR9310002495.
J. Buckingham and S.M. Donghy, Dictionary of Organic Compounds, Chapman and Hall, New York, edn. 5 (1982).