Contribution of microwaves in organic synthesis: statement of a methodology for the microwave-induced preparation of benzofuran-2(3H )-one and its comparison with classical heating

Abstract

The intramolecular cyclisation of 2-hydroxyphenylacetic acid 1 into coumaran-2-one 2 was studied under both microwave irradiation and classical heating for comparison purposes. The use of a monomode oven allowed an accurate consideration of the temperature distribution in the microwave reaction vessel, which revealed a very strong and unexpected thermal heterogeneity. The reaction was facilitated by the presence of a trace of toluene-p-sulfonic acid, the catalytic role of which is demonstrated.

References

1. R. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge and J. Rousell, Tetrahedron Lett., 1986, 27, 279.
2. R. Giguere, T. Bray, S. Duncan and G. Majetich, Tetrahedron Lett., 1986, 27, 4945.
3. A. Bose, M. Manhas, M. Manta-Shah, V. Raju, S. Bari, S. Newaz, B. Banik, A. Chaudhary and K. Barakat, J. Org. Chem., 1991, 56, 6968 (“MORE” Chemistry is “Microwave-Induced Organic Reaction Enhancement Chemistry”).
4. A. Bose, M. Manhas, B. Banik and E. Robb, Res. Chem. Intermed., 1994, 20, 1.
5. D. Villemin and B. Labiad, Synth. Commun., 1990, 20, 3333.
6. G. Bram, A. Loupy and M. Madjoub, Tetrahedron, 1990, 46, 5167.
7. D. Villemin and A. Ben Alloum, Synth. Commun., 1991, 21, 63.
8. D. Villemin, B. Martin and B. Garrigues, Synth. Commun., 1993, 23, 2251.
9. D. Jinchang, G. Hengjie, W. Jinzhu and L. Caizhen, Synth. Commun., 1994, 24, 301.
10. D. Abenhaïm, C. Ngoc-Son, A. Loupy and N. Ba-Hiep, Synth. Commun., 1994, 24, 1199.
11. D. Villemin and B. Martin, J. Chem. Res. (S), 1994, 146.
12. G. Bram, A. Loupy, M. Madjoub and A. Petit, Chem. Ind. (London), 1991, 396.
13. J. F. Pilard, B. Klein, F. Texier-Boullet and J. Hamelin, Synlett, 1992, 219.
14. J. M. Lerestif, J. Perrocheau, F. Tonnard, J. P. Bazureau and J. Hamelin, Tetrahedron, 1995, 51, 6757.
15. U. Fernandez-Paniagua, B. Illescas, N. Martin, C. Seoane, P. De La Cruz, A. De La Hoz and F. Langa, J. Org. Chem., 1997, 62, 3705.
16. D. Villemin, M. Hachemi and M. Lalaoui, Synth. Commun., 1996, 26, 2461.
17. G. Nagy, S. Filip, E. Surducan and V. Surducan, Synth. Commun., 1997, 27, 3736.
18. A. Souadi, J. Hamelin and H. Benhaoua, Tetrahedron Lett., 1998, 39, 4035 and cited references.
19. A. Diaz-Ortiz, E. Diez-Barra, A. De La Hoz, A. Loupy, A. Petit and L. Sanchez, Heterocycles, 1994, 38, 795.
20. R. Saillard, M. Poux and M. Audhuy-Peaudecerf, Mater. Res. Soc. Symp. Proc., 1996, 403, 411.
21. A. Loupy, D. Monteux, A. Petit, J. Aizpurua, E. Dominguez and C. Palomo, Tetrahedron Lett., 1996, 37, 8177.
22. S. Rigolet, P. Goncalo, J. M. Melot and J. Vebrel, J. Chem. Res. (M), 1998, 2813.
23. C. Roussel, K. Ciamala and J. Vebrel, unpublished work.
24. M. Msaddek, M. Rammah, K. Ciamala, J. Vebrel and B. Laude, Synthesis, 1997, 1495.
25. P. Pfeiffer and K. Bauer, Chem. Ber., 1947, 80, 7.
26. H. Holmquist, J. Org. Chem., 1969, 34, 4164.
27. T. Fukagawa, Y. Fujiwara and H. Tanigushi, J. Org. Chem., 1982, 47, 2471.
28. E. Gutierrez, A. Loupy, G. Bram and E. Ruiz-Hitsky, Tetrahedron Lett., 1989, 30, 945.
29. H. Kissinger, J. Res. Nat. Bur. Stand., 1956, 57, 217.
30. M. Cizmeciogly and A. Gupta, SAMPE Q., 1982, 16.
31. B. George, Thèse de Chimie Physique, Université de Besançon, 1997.
32. P. Murray and J. White, Trans. Br. Ceram. Soc., 1955, 54, 204.
33. J. March, Advanced Organic Chemistry, Wiley, New York, 3rd edition, 1985, p. 72.
34. W. Hemminger, Calorimetry and Thermal Analysis of Polymers, V. B. F. Mathot, München, 1976, ch. 2.
35. Dictionary of Organic Compounds, Chapman and Hall, New York, 5th edition, 1982, vol. 1, p. 558.