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

liquid Liquid is a state of matter with a definite volume but no fixed shape. Liquids adapt to the shape of their container and are nearly incompressible, maintaining their volume even under pressure. The density of a liquid is usually close to th ...

with a honey-like odor.

Synthesis

It is prepared by the

aldol condensation An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde or β-hydroxyketone (an aldol reaction), and this is then followed by dehydration t ...

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

to give

diacetone alcohol Diacetone alcohol is an organic compound with the formula CH3C(O)CH2C(OH)(CH3)2, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent. Synthesi ...

, which readily dehydrates to give this compound. :

Phorone Phorone, or diisopropylidene acetone, is a yellow crystalline substance with a geranium odor, with formula or . Preparation It was first obtained in 1837 in impure form by the French chemist Auguste Laurent, who called it "camphoryle". In 1849, ...

and

isophorone Isophorone is an Alpha-beta Unsaturated carbonyl compounds, α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precu ...

may be formed under the same conditions. Isophorone originates via a

Michael addition In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a c ...

: :

is formed by continued aldol condensation: : Phoron formation

Uses

Mesityl oxide is used as a solvent and in the production of

methyl isobutyl ketone Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the structural formula, condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes ...

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

: :

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

Dimedone Dimedone is an organic compound with the formula . Classified as a cyclic diketone, it is a derivative of 1,3-Cyclohexanedione, 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used a ...

is another established use of mesityl oxide.

References

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External links

IPCS INCHEM Description
Enones Ketone solvents