7440. Pinacolone

Nomenclature

CAS number: 75-97-8
3,3-Dimethyl-2-butanone; tert-butyl methyl ketone; pinacolin.
C6H12O; mol wt 100.16.
C 71.95%, H 12.08%, O 15.97%.

Description and references

Prepd by distillation of pinacol hydrate with dil H2SO4: Fittig, Ann. 114, 56 (1860); Hill, Flosdorf, Org. Synth. coll. vol. I (2nd ed., 1941) p 462; L. F. Fieser, K. L. Williamson, Organic Experiments (D. C. Heath and Co., Lexington, Mass., 5th ed., 1983) p 332. Almost quantitative yields are obtained when 56.5 g pinacol hydrate is boiled for 3 hrs with 0.5 liter 25% H2SO4 and the product is steam distilled: Boeseken, van Tonningen, Rec. Trav. Chim. 39, 189 (1920).

Chemical structure

Properties

Liquid. Peppermint or camphor-like odor. d2525 0.7250. mp -52.5°. bp760 106.2°. nD25 1.3939. Volatile in steam. Moderately sol in water (2.44% at 15°). Soluble in alcohol, ether, acetone.

Derivative

Oxime.
C6H13NO; mol wt 115.17.
C 62.57%, H 11.38%, N 12.16%, O 13.89%.

Properties

Needles from aq alcohol. mp 78°. bp748 171.6°. Sol in alc, ether, petr ether, benzene, chloroform.