Mesityl oxide

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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.[1]

Synthesis

It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates to give this compound.[2][3]

File:Acetone mesityl oxide.png

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

File:Isophorone mesityl oxide.png

Phorone is formed by continued aldol condensation:

File:Phoron formation.svg

Uses

Mesityl oxide is used as a solvent and in the production of methyl isobutyl ketone by hydrogenation:[3]

File:Hydrogenation of mesityl oxide to MIBK.png

Further hydrogenation gives 4-methyl-2-pentanol (methyl isobutyl carbinol).

Dimedone is another established use of mesityl oxide.

References

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External links

  1. Merck Index, 14th Edition
  2. Template:OrgSynth
  3. a b Script error: No such module "citation/CS1".