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

liquid A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, a ...

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 to ...

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

to give diacetone alcohol, 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 precur ...

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

Michael addition In organic chemistry, the Michael reaction or Michael 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 carbon ...

: :

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) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and ...

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

: :

Further hydrogenation gives

4-methyl-2-pentanol 4-Methyl-2-pentanol (IUPAC name: 4-methylpentan-2-ol) or methyl isobutyl carbinol (MIBC) is an organic chemical compound used primarily as a frother in mineral flotation and in the production of lubricant oil additives such as Zinc dithiophosph ...

(methyl isobutyl carbinol).

Dimedone Dimedone is a cyclic diketone used in organic chemistry to determine whether a compound contains an aldehyde group. Cyclohexanediones in general can be used as catalysts in the formation of transition-metal complexes. Other uses include applicatio ...

is another established use of mesityl oxide.

References

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External links

IPCS INCHEM Description
Enones Ketone solvents