Propiophenone (

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

: 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 ...

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

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

organic solvent A solvent (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 organic reaction, reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an Aromatic hydrocarbon, aromatic ring. Friedel–Crafts reactions are of two main types: alky ...

propanoyl chloride Propionyl chloride (also propanoyl chloride) is the organic compound with the formula CH3CH2C(O)Cl. It is the acyl chloride derivative of propionic acid. It undergoes the characteristic reactions of acyl chlorides. It is a colorless, corrosive, v ...

and

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

. It is also prepared commercially by

ketonization Ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction involving decarboxylation, converting two equivalents of a carboxylic acid () to a symmetric ketone (). The reaction typically requires heat and a ...

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. The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which ...

and

propionic acid Propionic acid (, from the Greek language, 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 . It is a ...

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 Aluminium oxide (or aluminium(III) oxide) is a chemical compound of aluminium and oxygen with the chemical formula . It is the most commonly occurring of several aluminium oxides, and specifically identified as aluminium oxide. It is commonly ...

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.">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. Other drugs made from propiophenone include the following: PDM-35, Eprazinone, Methcathinone (leading to ephedrine), Trimebutine, [ mfepramone,

Diphepanol Diphepanol is a cough medicine, cough suppressant (antitussive). Synthesis Ex 1: The α-keto bromination of propiophenone 3-55-0(1) gives 2-bromopropiophenone 114-00-3(2). Displacement of the halogen and hence amination with piperidine ...

, Metamfepramone"> ...

Production

Uses

References