Jones oxidation

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The Jones oxidation is a chemical reaction described as the chromic acid oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively.^{[1][2][3][4][5]} Jones reagent - a solution of chromic acid in concentrated sulfuric acid - is used as the oxidizing agent

The solvent acetone markedly affects the properties of the chromic acid. The oxidation is very rapid, quite exothermic, and the yields are typically high. The reagent rarely oxidizes unsaturated bonds.

Unfortunately, the chromium residue is very toxic, and care must be taken to dispose of it properly.

[edit] References

1. ↑  Bowden, K.; Heilbron, I. M.; Jones, E. R. H. J. Chem. Soc. 1946, 39.
2. ↑  Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F. J. Chem. Soc. 1949, 604.
3. ↑  Bladon, P. et al. J. Chem. Soc. 1951, 2402.
4. ↑  Jones, E. R. H. et al. J. Chem. Soc. 1953, 457 & 2548 & 3019.
5. ↑  Djerassi, C. et al. J. Org. Chem. 1956, 21, 1547.
6. Ley, S. V.; Madin, A. Comp. Org. Syn. 1991, 7, 253-256. (Review)
7. Organic Syntheses, Coll. Vol. 5, p.310 (1973); Vol. 45, p.28 (1965). (Article)
8. Organic Syntheses, Coll. Vol. 5, p.866 (1973); Vol. 45, p.77 (1965). (Article)

[edit] See also

• Collins reagent
• Pyridinium chlorochromate
• Sarett oxidation