The oxidation of aldehydes to methyl esters using trichloroisocyanuric acid

Synthetic Communications

Volumn 26, Issue 14, 1996, Pages 2633-2639

  Hiegel, Gene A ^a   Bayne, Christopher D ^a   Donde, Yariv ^a   Tamashiro, Gerald S ^a   Hilberath, Lisa A ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030014770     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004579     Document Type: Article

References (9)

1. Larock, R.C., "Comprehensive Organic Transformations," VCH Publishers, New York, 1989; pp. 840-841.
2. For synthetic applications of 1 see: Hiegel, G.A. In "Encyclopedia of Reagents for Organic Synthesis;" Raquette, L.A., Ed.; Wiley: Chichester, Sussex, England, 1995; Vol. 7, p. 5072.
3. Secondary alcohols are oxidized rapidly by 1, primary alcohols more slowly, and methanol even more slowly; Hiegel, G.A. and Nalbandy, M., Synth. Commun., 1992, 22, 1595.
4. Although ketones are chlorinated by 1, with acetone as the solvent this was not a problem under the oxidation conditions used; Hiegel, G.A. and Peyton, K.B., Synth. Commun., 1985, 15, 385.
5. Hiegel, G.A., Abdala, M.H., Burke, S.V., and Beard, D.P., J. Chem. Ed., 1987, 64, 156.
6. As with other strong oxidizing agents, 1 should be added to the solvent rather than the solvent to 1 otherwise a violent reaction could occur.
7. The time between mixing the chemicals in the reaction flask and adding 1 was in the range of 3-38 min for all reactions.
8. During this process, wet iodide-starch test paper was used to periodically test for the presence of oxidizing power.
9. Diethyl ether was added instead of pentane in most cases.