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Diacetone alcohol

Diacetone alcohol

IUPAC name	4-Hydroxy-4-methyl-pentan-2-one
Other names	2-Pentanone, 4-hydroxy-4-methyl; 4-Hydroxy-2-keto-4-methylpentane; Diacetone alcohol
Identifiers
CAS number	123-42-2
RTECS number	SA9100000
SMILES	CC(=O)CC(C)(C)O
Properties
Molecular formula	C₆H₁₂O₂
Molar mass	116.16 g/mol
Appearance	Colorless liquid
Density	0.938 g/mL
Melting point	- 47 °C
Boiling point	166 °C
Solubility in water	moderate
Solubility	most organic solvents
Hazards
Main hazards	Flammable
R-phrases	R36
S-phrases	S24/25
Related Compounds
Related compounds	Acetone, methyl isobutyl ketone
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Diacetone alcohol is a chemical compound with the formula CH₃C(O)CH₂C(OH)(CH₃)₂. This liquid is common synthetic intermediate used for the preparation of other compounds.

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It is a natural ingredient of Sleepy grass (Achnatherum robustum).

Synthesis

First identified by Heintz^[1], its preparation entails the Ba(OH)₂-catalyzed condensation of two molecules of acetone^[2] It undergoes dehydration to give the α,β-unsaturated ketone, mesityl oxide:^[3] Hydrogenation of mesityl oxide gives the industrial solvent, methyl isobutyl ketone ("MIBK").

References

^ Heintz, Ann. 169, 114 (1873)
^ Conant, J. B.; Tuttle, N. (1941). "Diacetone Alcohol". Org. Synth.; Coll. Vol. 1: 199.
^ Conant, J. B.; Tuttle, N. (1941). "Mesityl Oxide". Org. Synth.; Coll. Vol. 1: 345.