Propiophenone (

shorthand Shorthand is an abbreviated symbolic writing method that increases speed and brevity of writing as compared to longhand, a more common method of writing a language. The process of writing in shorthand is called stenography, from the Greek ''ste ...

: benzoylethane or BzEt) is an

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

. It is a colorless, sweet-smelling liquid that is insoluble in water, but miscible with

organic solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...

s. It is used in the preparation of other compounds.

Production

Propiophenone can be prepared by

Friedel–Crafts reaction The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions ...

of propanoyl chloride and

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

. It is also prepared commercially by

ketonization In organic chemistry, ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction and a decarboxylation converting two equivalents of a carboxylic acid () to a symmetric ketone () by the application of heat w ...

benzoic acid Benzoic acid is a white (or colorless) solid organic compound with the formula , whose structure consists of a benzene ring () with a carboxyl () substituent. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, wh ...

and

propionic acid Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a liq ...

over

calcium acetate Calcium acetate is a chemical compound which is a calcium salt of acetic acid. It has the formula Ca(C2H3O2)2. Its standard name is calcium acetate, while calcium ethanoate is the systematic name. An older name is acetate of lime. The anhydrous ...

and alumina at 450–550 °C: :C₆H₅CO₂H + CH₃CH₂CO₂H → C₆H₅C(O)CH₂CH₃ + CO₂ + H₂O Ludwig Claisen discovered that α-methoxystyrene forms this compound when heated for an hour at 300 °C (65% yield).

Uses

120px, left, Phenmetrazine,_derived_from_propiophenone,_is_an_appetite_suppressant..html" ;"title="appetite_suppressant.html" ;"title="Phenmetrazine, derived from propiophenone, is an appetite suppressant">Phenmetrazine, derived from propiophenone, is an appetite suppressant.">appetite_suppressant.html" ;"title="Phenmetrazine, derived from propiophenone, is an appetite suppressant">Phenmetrazine, derived from propiophenone, is an appetite suppressant. It is an intermediate in the synthesis of the pharmaceuticals phenmetrazine and propoxyphen.

References

{{Reflist Aromatic ketones Phenyl compounds