Microwave-assisted oxidation of alcohols using aqueous hydrogen peroxide

Synlett

Volumn , Issue 1, 2000, Pages 143-145

  Bogdał, Dariusz ^a   Łukasiewicz, Marcin ^a  

^a CRACOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Alcohols; Biphasic system; Hydrogen peroxide; Microwave irradiation; Oxidation

Indexed keywords

ALCOHOL; CARBOXYLIC ACID DERIVATIVE; HYDROGEN PEROXIDE; KETONE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; MICROWAVE RADIATION; OXIDATION; REACTION TIME;

EID: 0033977506     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Trost, B.M., Ed.; Comprehensive of Organic Synthesis (Oxidation), Ed.; Pergamon: New York, Vol. 7, 1991
2. Hudlicky, M., Oxidations in Organic Chemistry, ACS Monographs 186: Washington, DC 1990.
3. a) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831;
4. b) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553.
5. a) Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281, 1646;
6. b) Sato, K.; Aoki, M.; Tagaki, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386.
7. a) Bogdal, D. J. Chem. Res. (S) 1998, 468;
8. b) Bogdal, D.; Pielichowski, J.; Jaskot, K. Org. Prep. Proc. Int. 1998, 30, 427;
9. c) Bogdal, D.; Pielichowski, J.; Boron, A. Synth. Commun. 1998, 28, 3029;
10. d) Bogdal, D.; Pielichowski, J.; Jaskot. K. Heterocycles 1997, 45, 715;
11. e) Bogdal, D.; Pielichowski, J.; Jaskot, K. Synth. Commun. 1997, 27, 1553;
12. f) Bogdal, D.; Pielichowski, J.; Boron, A. Synlett 1996, 873.
13. For relevant papers and reviews on microwave assisted chemical reactions see: a) Abramovitch, R.A. Org. Prep. Proc. Int. 1991, 23, 683;
14. b) Majetich, G.; Hicks, R. J. Microwave Power Electromagn. Energy 1995, 30, 27;
15. c) Caddick, S. Tetrahedron 1995, 51, 10403;
16. d) Strauss, C.R.; Trainor, R.W. Aust. J. Chem. 1995, 48, 1665;
17. e) Varma, R.S. "Microwave Assisted Reactions under Solvent-free Dry Conditions" in Microwaves: Theory and Application in Material Processing IV, Clark, D.E.; Sutton, W.H.; Lewis, D.A., Eds., American Ceramic Society, Ceramic Transactions 1997, 80, 375;
18. f) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213;
19. g) Bogdal, D. Wiad. Chem. 1999, 53, 66;
20. h) Deshayes, S.; Liagre, M.; Loupy, A.; Luche J.L.; Petit, A. Tetrahedron 1999, 55, 10851;
21. i) Varma, R. S. Green Chem. 1999, 43;
22. j) Varma, R. S. Clean Products and Processes 1999, I, 132 and ref. cited therein.
23. a) McKillop, A.; Young, D.W., Synthesis 1979, 401 and 481;
24. b) Posner, G.H., Angew. Chem. 1978, 90, 521; Angew. Chem. Int. Ed. Engl. 1978, 17, 487;
25. b) Posner, G.H., Angew. Chem. 1978, 90, 521; Angew. Chem. Int. Ed. Engl. 1978, 17, 487;
26. c) Solid Supports and Catalysts in Organic Synthesis, Ed. Smith, K., Ellis Horwood: London, 1992;
27. d) Balogh, M., Laszlo, P. Organic Chemistry Using Clays, Springer: Berlin, 1993;
28. e) Clark, J.H., Catalysis of Organic Reactions by Supported Inorganic Reagents, VCH: New York, 1994.
29. a) Varma, R.S.; Dahiya, R. Tetrahedron Lett. 1997, 38, 2023;
30. b) Varma, R.S.; Saini, R.K.; Meshram H.M. Tetrahedron Lett. 1997, 38, 6525;
31. c) Varma, R.S.; Saini, R.K.; Tetrahedron Lett. 1998, 39, 1481;
32. d) Varma, R.S.; Saini, K.S.; Dahiya, R. Tetrahedron Lett. 1997, 38, 7823;
33. e) Varma, R.S.; Saini, K.S.; Dahiya, R. J. Chem. Res. (S) 1998, 120.
34. Qussaid, A.; Loupy, A., J. Chem. Res. (S) 1997, 342
35. Palombi, L.; Bonadies, F.; Scettri, A. Tetrahedron 1997, 53, 15867.
36. The experiments can be done in a household microwave oven provided that the oven has to be modified and equipped with an upright condenser. The use of condenser is obligatory because, as in the most oxidation process, without accurate temperature and power adjustment the reactor can go out of control.
37. 4 and evaporation of the solvent gave crude 2-octanone which was purified by Kugelrohr distillation. Yield 1.9 g (94%).
38. For example see: a) Neumann, R.; Khenkin, A.M., J. Org. Chem. 1994, 59, 7577;
39. b) Neumann, R.; Gara M., J. Am. Chem. Soc. 1995, 117, 5066;
40. c) Ducan, D.C; Chambers, R.C.; Hecht, E.; Hill, C.L. J. Am. Chem. Soc. 1995, 117, 681;
41. d) Ishii, Y.; Yamawaki, K.; Ura, T.; Yamada, H.; Yoshida, T.; Ogawa, M., J. Org. Chem. 1988, 53, 3587.