Acetone

[67-64-1]  · C3H6O  · Acetone  · (MW 58.08)

(widely used solvent; versatile synthetic reagent)

Alternate Name: 2-propanone.

Physical Data: mp -94 °C; bp 56.5 °C; d 0.788 g cm-3; fp -18 °C.

Solubility: sol water, alcohol; miscible with most organic solvents.

Form Supplied in: colorless liquid, widely available.

Handling, Storage, and Precautions: slightly toxic; central nervous system depressant; highly flammable liquid; vapors may form explosive mixtures with air; reacts vigorously with strong oxidizing and reducing agents.

Protection of Diols.

Both 1,2- and 1,3-diols can be protected as acetonides by reaction with acetone (eq 1).1 Acetonides are resistant to basic and nucleophilic reagents, and can be readily cleaved by aqueous acid.

Ketene Formation.

Ketene can be prepared by distillation of acetone through a combustion tube packed with pieces of heated porcelain.2 An improved method of ketene formation from acetone utilized a ketene lamp, which afforded an 80-90% yield of ketene from acetone.3 Another method, which utilized a pyrolyzing coil, has been reported.4

Photochemical Alkylation.

Cyclic ethers undergo an acetone-initiated photochemical addition to terminal alkenes (eq 2).5 The reaction can be photochemically induced without ketone initiation; however, the ketone-initiated reactions are faster and higher yields are obtained. The photosensitized amidation of aromatic substrates in acetone has been reported.6

Oxidations.

Acetone is widely utilized as a solvent for the oxidation of trimethylsilyl ethers to ketones,7 alcohols to ketones,8 alcohols to acids,9 alkynes to diones,10 aldehydes to acids,11 and alkynic carbinols to alkynic ketones.8

Solvent for the Formation of Alkyl Iodides.

Alkyl iodides can be prepared from chlorides and bromides by utilizing Sodium Iodide in acetone. The reaction (sometimes called the Finkelstein reaction) is an equilibrium which is driven by the precipitation of sodium chloride or sodium bromide.12 This methodology has also been utilized to synthesize alkyl halides from sulfonates,13 phosphinates,14 and selenonates.15

Regeneration of Ketones.

Acetone undergoes an exchange reaction with tosylhydrazones to regenerate ketones in high yields (eq 3).16 This mild method has been applied to the regeneration of ketones from oximes,17 arylhydrazones,17 and thiazolidines.18

Related Reagents.

2,2-Dimethoxypropane; 2-Methoxypropene.


1. Skattebol, L.; Stenstom, Y.; Stjerna, M. ACS 1988, B42, 475.
2. Hurd, C. OSC 1941, 1, 330.
3. Hurd, C.; Williams, J. JOC 1940, 5, 122.
4. Reid, J.; Hannalainen, C. J. Ind. Eng. Chem. 1949, 41, 1018.
5. Rosenthal, I.; Elad, D. T 1967, 23, 3193.
6. Elad, D. TL 1963, 77.
7. Baker, R.; Rao, V. B.; Ravenscroft, P. D.; Swain, C. J. S 1983, 572.
8. Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. JCS 1946, 39.
9. Britcher, S.; Baumgarten, W.; Loeffler, L. JMC 1970, 926.
10. Srinivasan, N. S.; Lee, D. G. JOC 1979, 1574.
11. Barton, D. H. R.; Boar, R. B.; Widdowson, D. A. JCS 1970, 1208.
12. Abraham, E.; Smith, J. JCS 1936, 1605.
13. Eglinton, G.; Whiting, M. JCS 1950, 3650.
14. Bowers, W.; Findlay, J.; MacKay, W. JCS(C) 1970, 2631.
15. Krief, A.; Dumont, W.; Denis, J.-N. CC 1985, 571.
16. Sacks, C. E.; Fuchs, P. L. S 1976, 456.
17. Maynez, S.; Pelavin, L.; Erker, G. JOC 1975, 40, 3302.
18. Djerassi, C.; Crossley, N.; Kielczewski, M. A. JOC 1962, 27, 1112.

Roger Harrington

Ciba-Geigy, Summit, NJ, USA



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