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Mesityl oxide

Isobutenyl methyl ketone Methyl isobutenyl ketone Isopropylidene acetone 9000 mg/m3 (rat, 4 hr) 10,000 mg/m3 (mouse, 2 hr) 2000 mg/m3 (guinea pig, 7 hr) 1000 mg/kg (rabbit, oral) 710 mg/kg (mouse, oral) acetone, benzylideneacetone

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.

:[[Image:Acetone mesityl oxide.png|400px]]

Phorone and isophorone may be formed under the same conditions. Isophorone originates via a Michael addition:

:[[File:Isophorone mesityl oxide.png|350px]]

Phorone is formed by continued aldol condensation:

:[[File:Phoron formation.svg|frameless|500px]]

Uses

Mesityl oxide can be converted into methyl isobutyl ketone by palladium-catalyzed hydrogenation: :[[File:Hydrogenation of mesityl oxide to MIBK.png|250px]] Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).

Dimedone is another established use of mesityl oxide.

Mesityl oxide also finds use in the synthesis of Diacetonamine [625-04-7], which itself finds application in synthesis of Eucaine & α-Eucaine.

References

References

  1. {{PGCH. 0385
  2. {{IDLH. 141797. Mesityl oxide
  3. ''[[Merck Index]]'', 14th Edition
  4. (1921). "Mesityl Oxide".
  5. (2000). "Ullmann's Encyclopedia of Industrial Chemistry".
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enones ketone-solvents
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