Foeniculum

by | Mar 21, 2018 | Foeniculum

How Can We Help?
You are here:
< Back

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:[1]

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).[2][3]

Uses

Propiophenone is used in the synthesis of a variety of pharmaceutical drugs:[1][4][5]

For example, SK&F 70463-A has a mixture of stimulant as well as depressant properties.

  1. Cathinone derivatives, e.g. Methcathinone, Metamfepramone, Amfepramone, Ethcathinone & α-PPP [19134-50-0].
  2. Ephedrine & Norephedrine.
  3. Phenmetrazine & phendimetrazine & PDM-35.
  4. Dextropropoxyphene & Pyrrolifene (sp. Pyrroliphene)
  5. Diphepanol
  6. Etoxadrol
  7. Eprazinone
  8. Hydroxyphenamate
  9. Trimebutine & Fedotozine
  10. Oxifenamate
  11. Flumecinol
  12. Iminophenimide
  13. Bencisteine
  14. Perisone
  15. CID:67948865 (Hungarian nootropic):[6]
  16. SK&F 70463-A HCl: [1477-79-8] Ref:[7] Patent:[8]
  17. R 1204 & R 960[9]
  18. alpha,alpha-Diphenyl-beta-methyl-1-pyrrolidinepropanol [2260-35-7]

References

  1. ^ a b Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3527306732.
  2. ^ Claisen, Ludwig (1896). "Ueber eine eigenthümliche Umlagerung" [On a peculiar rearrangement]. Berichte der Deutschen Chemischen Gesellschaft. 29 (3): 2931–2933. doi:10.1002/cber.189602903102.
  3. ^ Spielman, M. A.; Mortenson, C. W. (1940). "The Condensation of α-Methoxystyrene with Halogen Compounds". Journal of the American Chemical Society. 62 (6): 1609–1610. doi:10.1021/ja01863a076.
  4. ^ "propiophenone". Merriam-Webster.com. Merriam-Webster. Retrieved 2 June 2012.
  5. ^ Hartung, Walter H.; Crossley, Frank (1936). "Isonitrosopropiophenone". Organic Syntheses. 16: 44. doi:10.15227/orgsyn.016.0044.
  6. ^ Karoly Nador, et al. WO1991008200 ().
  7. ^ Barron, D. I.; Hall, G. H.; Natoff, I. L.; Vallance, D. K. (1965). "Pharmacological properties of 3-dimethylamino-2-methyl-1-phenyl-1-o-tolylpropanol (SK&F 70463-A)". Journal of Pharmacy and Pharmacology. 17 (8): 509–516. doi:10.1111/j.2042-7158.1965.tb07713.x
  8. ^ Robert Geoffrey Willi Spickett, et al. GB1039454 (1966 to Smith Kline and French Laboratories Ltd).
  9. ^ Janssen, Paul; Jageneau, Anton H. M.; Demoen, Paul J. A.; van De Westeringh, Corn.; De Canniere, Julienne H. M.; Raeymaekers, Alfons H. M.; Wouters, Maria; Sanczuk, Stefan; Hermans, Bert K. F. (1960). "Compounds Related to Pethidine--III. Basic Ketones derived from Norpethidine". Journal of Medicinal and Pharmaceutical Chemistry. 2 (3): 271–280. doi:10.1021/jm50010a003.
Categories
Table of Contents