Simple and improved procedure for regioselective acylation of aromatic ethers with carboxylic acids on the solid surface of alumina in the presence of trifluoroacetic anhydride

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9546-9547

  Ranu, Brindaban C ^a   Ghosh, Keya ^a   Jana, Umasish ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001522479     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615413     Document Type: Article

References (33)

1. (a) Olah, G. A. Friedel - Crafts and Related Reactions; Interscience: New York, 1964; Vol. III, Part 1.
2. (b) Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 753.
3. (a) Nomita, K.; Sugaya, Y.; Sasa, S.; Miwa, M. Bull. Chem. Soc. Jpn. 1980, 53, 2089.
4. (b) Yamaguchi, T.; Mitoh, A.; Tanabe, K. Chem. Lett. 1982, 1229.
5. (c) Mukaiyama, T.; Nagaoka, H.; Ohshima, M.; Murakami, M. Chem. Lett. 1986, 165.
6. (d) Mukaiyama, T.; Ohno, T.; Nishimura, T.; Han, S. J.; Kobayashi, S. Chem. Lett. 1991, 1059.
7. (e) Mukaiyama, T.; Suzuki, K.; Han, S. J.; Kobayashi, S. Chem. Lett. 1992, 432.
8. (f) Kawada, A.; Mitamura, S.; Kobayashi, S. Synlett 1994, 545.
9. (g) Hachiya, I.; Moriwaki, M.; Kobayashi, S. Bull. Chem. Soc. Jpn. 1995, 68, 2053.
10. (h) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
11. Schiemenz, G. P.; Schmidt, U. Liebigs Ann. Chem. 1976, 1514.
12. (a) Chiche, B.; Finiels, A.; Gauthier, C.; Geneste, P. J. Org. Chem. 1986, 51, 2128.
13. (b) Wang, Q. L.; Ma, Y.; Ji, X.; Yan, H.; Qiu, Q. J. Chem. Soc., Chem. Commun. 1995, 2307.
14. (a) Ranu, B. C.; Bhar, S.; Sarkar, D. C. Tetrahedron Lett. 1991, 32, 2811.
15. (b) Ranu, B. C.; Bhar, S. Tetrahedron 1992, 48, 1327.
16. (c) Ranu, B. C.; Bhar, S.; Chakrabori, R. J. Org. Chem. 1992, 57, 7349.
17. (d) Ranu, B. C.; Bhar, S. J. Chem. Soc., Perkin Trans. 1 1992, 365.
18. (e) Ranu, B. C.; Sarkar, D. C.; Chakraborty, R. Synth. Commun. 1992, 22, 1095.
19. (f) Ranu, B. C.; Saha, M.; Bhar, S. Tetrahedron Lett. 1993, 34, 1989.
20. (g) Ranu, B. C.; Chakraborty, R. Tetrahedron 1993, 49, 5333.
21. (h) Ranu, B. C.; Chakraborty, R.; Saha, M. Tetrahedron Lett. 1993, 34, 4659.
22. (i) Ranu, B. C.; Saha, M.; Bhar, S. J. Chem. Soc., Perkin Trans. 1 1994, 2197.
23. (j) Ranu, B. C.; Saha, M. J. Org. Chem. 1994, 59, 8269.
24. (k) Ranu, B. C.; Majee, A.; Das, A. R. Synth. Commun. 1995, 25, 363.
25. (l) Ranu, B. C.; Sarkar, A.; Saha, M.; Bhar, S. Pure Appl. Chem. 1996, 68, 775.
26. (m) Ranu, B. C.; Saha, M.; Bhar, S. Synth. Commun., in press.
27. Bourne, E. J.; Stacey, M.; Tatlow, J. C.; Tedder, J. M. J. Chem. Soc. 1951, 719.
28. Pouchert, C. J. The Aldrich Library of NMR Spectra, 2nd ed.; Aldrich Chemical Co., Inc.: Milwaukee, 1983; Vol. 2.
29. Effenberger, F.; Epple, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 300.
30. Matsuda, S.; Ogawa, M.; Okazaki, T.; Benden, M. M. Chem. Abst. 1958, 52, 10930f.
31. 2: C, 77.02; H, 8.31. Found: C, 76.91; H, 8.12.
32. Awad, W. I.; EL-Neweihy, M. F.; Selin, S. F. J. Org. Chem. 1958, 23, 1783.
33. Mathur, K. B. L.; Sharma, J. N.; Venkataramanan, K.; Krishnamurthy, H. G. J. Am. Chem. Soc. 1957, 79, 1957.