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Environment-Friendly, Mild and One-Step Synthesis of Safrole
Corresponding Author(s) : Hong Huang
Asian Journal of Chemistry,
Vol. 27 No. 3 (2015): Vol 27 Issue 3
Abstract
One-step synthesis of safrole, an important flavor compound, was described. Safrole was prepared by Friedel-Crafts reaction of 1,2-methylenedioxybenzene and allyl alcohol with recyclable Catalysts-Nafion-H. Safrole was obtained with a yield of 80 % and little isosafrole was obtained. The catalyst and excess raw material can be recycled and reused.
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- G.A. Olah, J. Kaspi and J. Bukala, J. Org. Chem., 42, 4187 (1977); doi:10.1021/jo00862a003.
- K. Arata, H. Nakamura and M. Shouji, Appl. Catal. A, 197, 213 (2000); doi:10.1016/S0926-860X(99)00484-6.
- G.A. Olah, R. Malhotra, S.C. Narang and J.A. Olah, Synthesis, 672 (1978); doi:10.1055/s-1978-24846.
- M.A. Harmer, W.E. Farneth and Q. Sun, J. Am. Chem. Soc., 118, 7708 (1996); doi:10.1021/ja9541950.
- D. Zhou, J. Yang, G. Dong, M. Huang and Y. Jiang, J. Mol. Catal. Chem., 159, 85 (2000); doi:10.1016/S1381-1169(00)00174-6.
- B. Török, I. Kiricsi, Á. Molnár and G.A. Olah, J. Catal., 193, 132 (2000); doi:10.1006/jcat.2000.2869.
- A.S. Lages, K.C.M. Silva, A.L.P. Miranda, C.A.M. Fraga and E.J. Barreiro, Bioorg. Med. Chem. Lett., 8, 183 (1998); doi:10.1016/S0960-894X(97)10216-5.
- A.C. Silva, E.S. Mendonça and C. Reis, Quim. Nova, 26, 344 (2003); doi:10.1590/S0100-40422003000300011.
- E.J. Barreiro and C.A.M. Fraga, Quim. Nova, 22, 744 (1999); doi:10.1590/S0100-40421999000500019.
- P.R.R Costa, C.C. Lopes, An. Acad. Brasil Cienc., 54, 758 (1982).
- E.J. Barreiro, P.R.R. Costa, P.R.V.R. Barros, W.M. Queiroz, J. Chem. Res. (S), 102 (1982).
- L.G. French, J. Chem. Educ., 72, 484 (1995); doi:10.1021/ed072p484.
- G.L. Chen, L. Yang, T.C. Rowe, B.D. Halligan, K. Tewey and L. Liu, J. Biol. Chem., 259, 13560 (1984).
- N. Tsukada, Y. Yagura, T. Sato and Y. Inoue, Synlett, 1431 (2003); doi:10.1055/s-2003-40859.
- B. Lin and X. Yang, Guangdong Huagong, 30, 6 (2003).
- S. Protti, M. Fagnoni and A. Albini, Org. Biomol. Chem., 3, 2868 (2005); doi:10.1039/b506735a.
- T. Yamato, C. Hideshima, G.K.S. Prakash and G.A. Olah, J. Org. Chem., 56, 2089 (1991); doi:10.1021/jo00006a023.
- B.R. Cho and H.J. Yang, Bull. Korean Chem. Soc., 12, 463 (1991).
References
G.A. Olah, J. Kaspi and J. Bukala, J. Org. Chem., 42, 4187 (1977); doi:10.1021/jo00862a003.
K. Arata, H. Nakamura and M. Shouji, Appl. Catal. A, 197, 213 (2000); doi:10.1016/S0926-860X(99)00484-6.
G.A. Olah, R. Malhotra, S.C. Narang and J.A. Olah, Synthesis, 672 (1978); doi:10.1055/s-1978-24846.
M.A. Harmer, W.E. Farneth and Q. Sun, J. Am. Chem. Soc., 118, 7708 (1996); doi:10.1021/ja9541950.
D. Zhou, J. Yang, G. Dong, M. Huang and Y. Jiang, J. Mol. Catal. Chem., 159, 85 (2000); doi:10.1016/S1381-1169(00)00174-6.
B. Török, I. Kiricsi, Á. Molnár and G.A. Olah, J. Catal., 193, 132 (2000); doi:10.1006/jcat.2000.2869.
A.S. Lages, K.C.M. Silva, A.L.P. Miranda, C.A.M. Fraga and E.J. Barreiro, Bioorg. Med. Chem. Lett., 8, 183 (1998); doi:10.1016/S0960-894X(97)10216-5.
A.C. Silva, E.S. Mendonça and C. Reis, Quim. Nova, 26, 344 (2003); doi:10.1590/S0100-40422003000300011.
E.J. Barreiro and C.A.M. Fraga, Quim. Nova, 22, 744 (1999); doi:10.1590/S0100-40421999000500019.
P.R.R Costa, C.C. Lopes, An. Acad. Brasil Cienc., 54, 758 (1982).
E.J. Barreiro, P.R.R. Costa, P.R.V.R. Barros, W.M. Queiroz, J. Chem. Res. (S), 102 (1982).
L.G. French, J. Chem. Educ., 72, 484 (1995); doi:10.1021/ed072p484.
G.L. Chen, L. Yang, T.C. Rowe, B.D. Halligan, K. Tewey and L. Liu, J. Biol. Chem., 259, 13560 (1984).
N. Tsukada, Y. Yagura, T. Sato and Y. Inoue, Synlett, 1431 (2003); doi:10.1055/s-2003-40859.
B. Lin and X. Yang, Guangdong Huagong, 30, 6 (2003).
S. Protti, M. Fagnoni and A. Albini, Org. Biomol. Chem., 3, 2868 (2005); doi:10.1039/b506735a.
T. Yamato, C. Hideshima, G.K.S. Prakash and G.A. Olah, J. Org. Chem., 56, 2089 (1991); doi:10.1021/jo00006a023.
B.R. Cho and H.J. Yang, Bull. Korean Chem. Soc., 12, 463 (1991).