A convenient chlorine-free procedure for the direct esterification of cinnamic acids with phenols is described. The method does not require stoichiometric activation of the carboxyl group with thionyl chloride or condensing reagents. The methodology is very simple, environmentally friendly, and high-yielding for both electron-releasing and -withdrawing substituted phenols. The Keggin heteropoly acids H3PMo12O40 and H4SiMo12O40 were employed as catalyst in simple bulk form. The effects of temperature, reaction time, and amount of the catalyst used on the ester yield were checked. Suitable conditions for the reaction include a 1:1 molar ratio of reactants and a 1 mmol % of catalyst to reactant ratio. Seventeen aryl cinnamates were obtained, yields ranged from 80 to 91 % for most of the esters. The catalyst was shown to be reusable for at least four times without any appreciable loss of its activity.
References
1 R. C. Larock. Comprehensive Organic Transformations, p. 966, VCH, New York (1989).Search in Google Scholar
2 J. Kim, Y. Park, D. Kweon, Y. Kang, H. Kim, S. Lee, S. Cho, W. Lee, Y. Yoon. Bull. Korean Chem. Soc.25, 501 (2004).Search in Google Scholar
3 A. R. Katritzky, O. Meth-Cohn, W. Charles. Comprehensive Organic Transformations, Vol. 5, Pergamon (1996).Search in Google Scholar
4 10.1080/17415990500031187, I. El-Sakkaa, N. Hassanb. J. Sulfur Chem.26, 33 (2005).Search in Google Scholar
5 10.1002/anie.200700590, Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao. Angew. Chem., Int. Ed.46, 5554 (2007).Search in Google Scholar
6 10.1016/S0040-4039(98)01750-X, K. Hirabayashi, Y. Nishihara, A. Mori, T. Hiyama. Tetrahedron Lett.39, 7893 (1998).Search in Google Scholar
7 10.1016/j.catcom.2011.01.008, J. Wei, H. Fu, R. Li, H. Chen, X. Li. Catal. Commun.12, 748 (2011).Search in Google Scholar
8 10.1627/jpi.46.105, T. Tagawa, J. Amemiya, G. Goto, S. Gakkaishi. J. Jpn. Pet. Inst.46, 105 (2008).Search in Google Scholar
9 10.1039/b109845b, P. Wasserscheid, M. Sesing, W. Korth. Green Chem.4, 134 (2002).Search in Google Scholar
10 T. Tagawa, J. Amemiya, S. Goto. Appl. Catal., A257, 19 (2004).10.1016/S0926-860X(03)00638-0Search in Google Scholar
11 10.1016/S0040-4039(02)00430-6, S. Ma, J. Zhang. Tetrahedron Lett.43, 3435 (2002).Search in Google Scholar
12 10.1016/S0040-4020(03)01026-3, S. Ma, J. Zhang. Tetrahedron59, 6273 (2003).Search in Google Scholar
13 10.1055/s-0029-1219927, P. Tundo, C. McElroy, F. Aricó. Synlett 1567 (2010).Search in Google Scholar
14 10.1039/b711197e, A. Ion, Ch. Van Doorslaer, V. Parvulescu, P. Jacobs, D. De Vos. Green Chem.10, 111 (2008).Search in Google Scholar
15 T. Zevaco, A. Janssen, E. Dinjus. Arkivociii, 51 (2007).10.3998/ark.5550190.0008.314Search in Google Scholar
16 10.1007/s10562-010-0394-0, F. Chen, T. Dong, Y. Chi, Y. Xu, Ch. Hu. Catal. Lett.139, 38 (2010).Search in Google Scholar
17 10.1039/b106201h, M. Abla, J. Choi, T. Sakakura. Chem. Commun. 2238 (2001).Search in Google Scholar
18 10.1016/j.bmcl.2004.05.069, S. Gobec, M. Sova, K. Kristan, T. Rizner. Bioorg. Med. Chem. Lett.14, 3933 (2004).Search in Google Scholar
19 10.1016/S0040-4020(99)00546-3, C. Pinto, A. Silva, A. Cavaleiro, J. Foces-Foces, A. Llamas-Saiz, N. Jegerovic. Tetrahedron55, 10187 (1999).Search in Google Scholar
20 10.1271/bbb.65.161, J. Zhu, M. Majikina, S. Tawata. Biosci. Biotechnol. Biochem.65, 161 (2001).Search in Google Scholar PubMed
21 E. Womack, J. McWhirter. Org. Synth. Coll.III, 714 (1955).Search in Google Scholar
22 10.1039/p29880000557, N. Isaacs, T. Najem. J. Chem. Soc., Perkin Trans. 2 557 (1988).Search in Google Scholar
23 R. Mali, A. Papalkar. J. Chem. Res. (S), 603 (2003).10.3184/030823503322655661Search in Google Scholar
24 D. Ruiz, G. Romanelli, D. Bennardi, G. Baronetti, H. Thomas, J. Autino. Arkivocvii, 269 (2008).10.3998/ark.5550190.0009.c29Search in Google Scholar
25 10.1016/j.cej.2009.12.029, G. Romanelli, D. Ruiz, P. Vázquez, H. Thomas, J. Autino. Chem. Eng. J.161, 355 (2010).Search in Google Scholar
26 G. Romanelli, P. Vázquez, L. Pizzio, N. Quaranta, J. Autino, M. Blanco, C. Cáceres. Appl. Catal., A261, 163 (2004).10.1016/j.apcata.2003.10.043Search in Google Scholar
27 L. Pizzio, G. Romanelli, P. Vázquez, J. Autino, M. Blanco, C. Cáceres. Appl. Catal., A308, 153 (2006).10.1016/j.apcata.2006.04.012Search in Google Scholar
28 G. Romanelli, J. Autino, P. Vázquez, L. Pizzio, M. Blanco, C. Cáceres. Appl. Catal., A352, 208 (2009).10.1016/j.apcata.2008.10.003Search in Google Scholar
29 10.1055/s-2008-1072502, P. Tundo, G. Romanelli, P. Vázquez, P. Loris, F. Aricó. Synlett 967 (2008).Search in Google Scholar
30 10.1016/j.catcom.2010.06.015, P. Tundo, G. Romanelli, P. Vázquez, F. Aricó. Catal. Commun.11, 1181 (2010).Search in Google Scholar
31 D. Bennardi, G. Romanelli, J. Autino. L. Pizzio, P. Vázquez, C. Cáceres, M. Blanco. React. Kinet., Mech. Catal.100, 165 (2010).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
