Jones oxidation

Jones oxidation

The Jones oxidation is a chemical reaction described as the chromic acid oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. [cite journal | author = Bowden, K.; Heilbron, I. M.; Jones, E. R. H | journal = J. Chem. Soc. | year = 1946 | pages = 39 | doi = 10.1039/jr9460000039 | title = 13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols] [cite journal | author = Heilbron, I.M.; Jones, E.R.H.; Sondheimer, F | journal = J. Chem. Soc. | year = 1949 | pages = 604 | doi = 10.1039/jr9490000604 | title = 129. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols] [cite journal | author = Bladon, P | journal = J. Chem. Soc. | year = 1951 | pages = 2402 | doi = 10.1039/jr9510002402 | title = 532. Studies in the sterol group. Part LII. Infra-red absorption of nuclear tri- and tetra-substituted ethylenic centres] [cite journal | author = Jones, E. R. H | journal = J. Chem. Soc. | year = 1953 | pages = 457 | doi = 10.1039/jr9530000457 | title = 92. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A] [cite journal | author = Jones, E. R. H | journal = J. Chem. Soc. | year = 1953 | pages = 2548 | doi = 10.1039/jr9530002548 | title = 520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C] [cite journal | author = Jones, E. R. H | journal = J. Chem. Soc. | year = 1953 | pages = 3019 | doi = 10.1039/jr9530003019 | title = 599. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A] [cite journal | author = C. Djerassi, R. Engle and A. Bowers | title = Notes - The Direct Conversion of Steroidal 5-3-Alcohols to 5- and 4-3-Ketones | year = 1956 | journal = J. Org. Chem. | volume = 21 | issue = 12 | pages = 1547–1549 | doi = 10.1021/jo01118a627] Jones reagent - a solution of chromium trioxide in concentrated sulfuric acid - is used as the oxidizing agent.

The Jones Reagent will also completely oxidize aldehydes to carboxylic acids.

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.

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

ee also

* Collins reagent
* Pyridinium chlorochromate
* Sarett oxidation

References

Further reading

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