The use of anhydrous CeCl3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones

Journal of the Brazilian Chemical Society

Volumn 21, Issue 2, 2010, Pages 371-374

  Silveira, Claudio C ^a   Mendes, Samuel R ^a   Ziembowicz, Francieli I ^a   Lenardão, Eder J ^b   Perin, Gelson ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF PELOTAS   (Brazil)

Author keywords

Acetals; Aldehydes; Cerium(III) chloride; Ketones; Trimethyl orthoformate

Indexed keywords

EID: 77951830760     PISSN: 01035053     EISSN: 16784790     Source Type: Journal    
DOI: 10.1590/S0103-50532010000200026     Document Type: Article

References (35)

1. th ed.; Wiley: New York, 2007, ch. 4;
2. Kocienski, P. J. In Protective Groups, 3rd ed.; Thieme: New York, 2004, ch. 2.
3. Yoshioka, S.; Oshita, M.; Tobisu, M.; Chatani, N.; Org. Lett. 2005, 7, 3697;
4. Lemiègre, L.; Stevens, R. L.; Combret, J.-C.; Maddaluno, J.; Org. Biomol. Chem. 2005, 3, 1308;
5. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T.; Org. Biomol. Chem. 2006, 4, 2337;
6. Li, L.-S.; Das, S.; Sinha, S. C.; Org. Lett. 2004, 6, 127.
7. Williams, D. B. G.; Lawton, M. C.; Green Chem. 2008, 10, 914.
8. Leonard, N. M.; Oswald, M. C.; Freiberg, D. A.; Nattier, B. A.; Smith, R. C.; Mohan, R. S.; J. Org. Chem. 2002, 67, 5202.
9. Smith, B. M.; Graham, A. E.; Tetrahedron Lett. 2006, 47, 9317.
10. Borujeni, K. P.; Massah, A. R.; React. Funct. Polym. 2006, 66, 1126.
11. Tsunoda, T.; Suzuki, M.; Noyori, R.; Tetrahedron Lett. 1980, 21, 1357.
12. Ono, F.; Inatomi,Y.; Tada, Y.; Mori, M.; Sato, T.; Chem. Lett.2009, 38, 96.
13. Luche, J.-L.; Gemal, A. L.; J. Chem. Soc., Chem. Commun. 1978, 976.
14. Gemal, A. L.; Luche, J.-L.; J. Org. Chem. 1979, 44, 4187.
15. Anderson, S. H.; Uh, H.-S.; Synth. Commun. 1973, 3, 125.
16. Bornstein, J.; Bedell, S. F.; Drummond, P. E.; Kopsloski, C. L.; J. Am. Chem. Soc. 1956, 78, 83.
17. Hamada, N.; Kazahaya, K.; Shimizu, H.; Sato, T.; Synlett 2004, 1074.
18. Roy, A.; Rahman, M.; Das, S.; Kundu, D.; Kundu, S. K.; Majee, A.; Hajra, A.; Synth. Commun. 2009, 39, 590.
19. Procuranti, B.; Connon, S. J.; Org. Lett. 2008, 10, 4935.
20. Cameron, A. F. B.; Hunt, J. S.; Oughton, J. F.; Wilkinson, P. A.; Wilson, B. M.; J. Chem. Soc. 1953, 3864.
21. Wenkert, E.; Goodwin, T. E.; Synth. Commun. 1977, 7, 409.
22. Kumar, D.; Kumar, R.; Chakraborti, A. K.; Synthesis 2008, 1249.
23. Zhou, W.; Xu, L.-W.; Yang, L.; Zhao, P.-Q.; Xia, C.-G.; J. Mol. Catal. A: Chem. 2006, 249, 129.
24. Kumar, R.; Kumar, D.; Chakraborti, A. K.; Synthesis 2007, 299.
25. Kantam, M. L.; Neeraja, V.; Sreekanth, P.; Catal. Commun. 2001, 2, 301;
26. Bailey, A. D.; Cherney, S. M.; Anzalone, P. W.; Anderson E. D.; Ernat, J. J.; Mohan, R. S.; Synlett 2006, 215;
27. Krishnaveni, N. S.; Surendra, K.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R.; J. Org.. Chem. 2003, 68, 2018;
28. Bailey, A. D.; Baru, A. R.; Tasche, K. K.; Mohan, R. S. Tetrahedron Lett. 2008, 49, 691.
29. Lenardão, E. J.; Trecha, D. O.; Ferreira, P. C.; Jacob, R. G.; Perin, G. J. Braz. Chem. Soc. 2009, 20, 93;
30. Perin, G.; Jacob, R. G.; Dutra, L. G.; Azambuja, F.; Santos, G. F. F.; Lenardão, E. J.; Tetrahedron Lett. 2006, 47, 935;
31. Lenardão, E. J.; Dutra, L. G.; Saraiva, M. T.; Jacob, R. G.; Perin, G.; Tetrahedron Lett. 2007, 48, 8011;
32. Lenardão, E. J.; Mendes, S. R.; Ferreira, P. C.; Perin, G.; Silveira, C. C.; Jacob, R. G.; Tetrahedron Lett. 2006, 47, 7439.
33. Silveira, C. C.; Mendes, S. R.; Tetrahedron Lett. 2007, 48, 7469.
34. Typical procedure for the synthesis of dimethyl acetals 2. To a mixture of trimethyl orthoformate (0.254 g, 2.2 mmol) and anhydrous CeCl3 (0.025 g, 0.1 mmol) at 0 °C under argon, was added benzaldehyde 1a (0.212 g, 2.0 mmol). The reaction progress was followed by TLC, and after stirring at 0 °C for 1.0 h (see Table 2) the starting materials were completely consumed. The resulting reaction mixture was quenched with saturated aqueous sodium bicarbonate solution followed by extraction with ethyl acetate (3 × 5 mL). After drying the organic phase over anhydrous MgSO4, the solvent was removed under reduced pressure to give the pure acetal 2a as a colorless oil (0.323g, 95%). 1H NMR (200 MHz, CDCl3): δ 7.45-7.43 (m, 2H), 7.36-7.29 (m, 3H), 5.38 (s, 1H), 3.31 (s, 6H).3l 13C NMR (50 MHz, CDCl3): δ 52.56, 103.09, 126.60, 128.08, 128.34, 137.99. When necessary, the residue was purified by column chromatography (ethyl acetate/hexanes 5/95).
35. Cerium chloride was dried according to: Dimitrov, V.; Kostova, K.; Genov, M.; Tetrahedron Lett. 1996, 37, 6787.