Jones Oxidation

Definition:

The oxidation of primary and secondary alcohols to acids and ketones, respectively, in the presence of chromic acid, aqueous sulfuric acid, and acetone.

Frequency of appearance:

   The periodicity of this reaction is not frequent enough to warrant a literature analysis.

Original reference:

1. K. Bowden et al., J. Chem. Soc. 1946, 39.

Recent academic references:

2. Direct Synthesis of 5-Substituted Naphthoquinones

• Kraus, G. A.; Kim, J.; J. Org. Chem.; 2002; 67(7); 2358-2360.

3. Synthesis of the C1-C13 Fragment of Leucascandrolide A

• Crimmins, M. T.; Carroll, C. A.; King, B. W.; Org. Lett.; 2000; 2(5); 597-599.

4. A Four-Step Synthesis of the Hydroazulene Core of Guanacastepene

• Dudley, G. B.; Danishefsky, S. J.; Org. Lett.; 2001; 3(15); 2399-2402.  

5. http://www.hut.fi/Yksikot/Orgaaninen/opetus/moderni_synteettinen/oxidat.pdf

6. Synthesis of Phenyl 1-Thioglycopyranosiduronic Acids using a Sonicated Jones Oxidation

• Nigel M. Allanson, Dashan Liu, Chi Feng, Rakesh K. Jain, Anna Chen, Manuka Ghosh, Liwu Hong and Michael J. SofiaTetrahedron Letters, Volume 39, Issue 14, 2 April 1998, Pages 1889-1892
  

Recent process references:

7. A Review of U.S. Patents in the Field of Organic Process Development Published during August to November, 2001

• Turner, K.; Org. Process Res. Dev.; 2002; 6(2); 98-108.  

 

Mechanism: http://www.sci.sdsu.edu/chemistry/CHEM231/231Lecture30.pdf

Scope and Limitations:

• Isolated double or triple bonds are not disturbed under these conditions. ^A
• Epimerization does not occur at adjacent chiral centers. ^A
• Conditons are usually aqueous sulfuric acid containing CrO₃ with the alcohol disolved in acetone.
• 1⁰ alcohols are oxidized to carboxylic acids (may isolate aldehyde if the inchoate product is distilled).
• 2⁰ alcohols are oxidized to ketones.
• Allylic alcohols may be oxidized to an aldehyde. ^A
• Goes by an E2 mechanism.

Synonyms: