Propiophenone Explained

Propiophenone (shorthand: benzoylethane or BzEt) is an aryl ketone. It is a colorless, sweet-smelling liquid that is insoluble in water, but miscible with organic solvents. It is used in the preparation of other compounds.

Production

Propiophenone can be prepared by Friedel–Crafts reaction of propanoyl chloride and benzene. It is also prepared commercially by ketonization of benzoic acid and propionic acid over calcium acetate 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).^{[1] [2]}

Uses

thumb|120px|left|Phenmetrazine, derived from propiophenone, is an appetite suppressant.It is an intermediate in the synthesis of the pharmaceuticals phenmetrazine and propoxyphen.^{[3] [4]}

Other drugs made from propiophenone include the following: PDM-35, Eprazinone, Methcathinone (leading to ephedrine), Trimebutine, Amfepramone, Diphepanol, Metamfepramone, Etoxadrol, Hydroxyphenamate, Phendimetrazine, Iminophenimide, Bencisteine, Flumecinol, Pyrroliphene, Perisone,

Notes and References

1. Claisen. Ludwig. Ueber eine eigenthümliche Umlagerung. On a peculiar rearrangement. Berichte der Deutschen Chemischen Gesellschaft. 1896. 29. 3. 2931–2933. 10.1002/cber.189602903102.
2. Spielman. M. A.. Mortenson. C. W.. The Condensation of α-Methoxystyrene with Halogen Compounds. Journal of the American Chemical Society. 1940. 62. 6. 1609–1610. 10.1021/ja01863a076.
3. Web site: propiophenone. Merriam-Webster.com. Merriam-Webster. 2 June 2012.
4. Organic Syntheses . Walter H. . Hartung. Frank . Crossley . Isonitrosopropiophenone . 1936. 16. 44. 10.15227/orgsyn.016.0044.