Hydrogen peroxide oxidation of aldehydes to carboxylic acids: An organic solvent-, halide- and metal-free procedure

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1439-1442

  Sato, Kazuhiko ^a   Hyodo, Mamoru ^a   Takagi, Junko ^a   Aoki, Masao ^a   Noyori, Ryoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Aldehydes; Baeyer Villiger reaction; Carboxylic acids; Hydrogen peroxide; Oxidation; Quaternary ammonium salts

Indexed keywords

ALCOHOL; ALDEHYDE DERIVATIVE; ALKENE; CARBOXYLIC ACID DERIVATIVE; HALIDE; HYDROGEN PEROXIDE; METAL; ORGANIC SOLVENT; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; OXIDATION; REACTION ANALYSIS;

EID: 0034716514     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02310-2     Document Type: Article

References (28)

1. (a) Hollingworth, G. J. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Elsevier Science: Oxford, 1995; Vol. 5, pp. 23-120.
2. (b) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph Ser. 186, American Chemical Society: Washington, DC, 1990; pp. 174-184.
3. (c) Larock, R. C. Comprehensive Organic Transformations; VCH Publishers: New York, 1989; pp. 838-841.
4. 3] Wuts, P. G.; Bergh, C. L. Tetrahedron Lett. 1986, 27, 3995-3998.
5. (b) [AgO+NaCN] Corey, E. J.; Gilman, N. W.; Ganem, B. J. Am. Chem. Soc. 1968, 90, 5616-5617.
6. (c) [Oxone] Kennedy, R. J.; Stock, A. M. J. Org. Chem. 1960, 25, 1901-1906.
7. 4] Ruhoff, J. R. Org. Synth., Coll. Vol. 1943, 2, 315-316.
8. 7] Hurd, C. D.; Garrett, J. W.; Osborne, E. N. J. Am. Chem. Soc. 1933, 55, 1082-1084.
9. 3] Moureu, C.; Chaux, R. Org. Synth., Coll. Vol. 1932, 1, 166-169.
10. 2, see: Yamada, T.; Rhode, O.; Takai, T.; Mukaiyama, T. Chem. Lett. 1991, 5-8.
11. 4] Venturello, C.; Gambaro, M. J. Org. Chem. 1991, 56, 5924-5931.
12. 2H] Choi, J.-K.; Chang, Y.-K.; Hong, S. Y. Tetrahedron Lett. 1988, 29, 1967-1970.
13. 2O] Trost, B. M.; Masuyama, Y. Tetrahedron Lett. 1984, 25, 173-176.
14. 2] Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567-569.
15. 2H] Dodd, R. H.; Hyaric, M. L. Synthesis 1993, 295-297.
16. 2CO] Ganem, B.; Heggs, R. P.; Biloski, A. J.; Schwartz, D. R. Tetrahedron Lett. 1980, 21, 685-688.
17. Späth, E.; Pailer, M.; Schmid, M. Chem. Ber. 1941, 74, 1552-1556.
18. Matsumoto, M.; Kobayashi, H.; Hotta, Y. J. Org. Chem. 1984, 49, 4740-4741.
19. Rémi, L.; Pierre, L.; Xiao, L.; Catherine, H. European Patent, 1991, 0 424 242 A2.
20. (a) Sato, K.; Aoki, M.; Takagi, J.; Zimmermann, K.; Noyori, R. Bull. Chem. Soc. Jpn. 1999, 72, 2287-2306.
21. (b) Sato, K.; Takagi, J.; Aoki, M.; Noyori, R. Tetrahedron Lett. 1998, 39, 7549-7552.
22. (c) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386-12387.
23. (d) Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281, 1646-1647.
24. 4a.
25. 4 at 25°C.
26. 3, and distilled through a short column to give 91.5 g (81%) of octanoic acid as a colorless liquid, b.p. 114.0-116.0°C/3 mmHg.
27. 2 epoxidation of olefins under aqueous/organic biphasic conditions, see: (a) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310-8311.
28. (b) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Panyella, D.; Noyori, R. Bull. Chem. Soc. Jpn. 1997, 70, 905-915.