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Perkin reaction

Organic reaction developed by William Henry Perkin

Perkin reaction
Summary

Organic reaction developed by William Henry Perkin

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin in 1868 that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid. The alkali salt acts as a base catalyst, and other bases can be used instead.

The Perkin reaction

Several reviews have been written.

Reaction mechanism

The Perkin reaction

Clear from the reaction mechanism, the anhydride of aliphatic acid must contain at least 2 α-H for the reaction to occur. The above mechanism is not universally accepted, as several other versions exist, including decarboxylation without acetic group transfer.

Applications

  • Salicylaldehyde converted to coumarin using acetic anhydride with acetate as base.
  • cinnamic acid is prepared from benzaldehyde, again using acetic anhydride in the presence of sodium or potassium acetate.
  • resveratrol (cf. fo-ti), a phytoestrogenic stilbene is yet another product of this methodology.

References

References

  1. Perkin, W. H.. (1868). "On the artificial production of coumarin and formation of its homologues". Journal of the Chemical Society.
  2. Perkin, W. H.. (1877). "On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues". Journal of the Chemical Society.
  3. (1950). "The nature of the catalyst in the Perkin condensation". J. Org. Chem..
  4. Johnson, J. R.. (1942). "The Perkin Reaction and Related Reactions". Org. React..
  5. House, H. O. (1972) ''Modern Synthetic Reactions'', W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663
  6. Rosen, T.. (1991). "The Perkin Reaction". Compr. Org. Synth..
  7. Bansal, Raj K. (1998) ''Organic Reaction Mechanisms'', Tata McGraw Hill, 3rd Edition , pp. 199–201, {{ISBN. 9780470858585 {{doi. 10.1002/0470858583.
  8. (2016). "Ullmann's Encyclopedia of Industrial Chemistry".
  9. (2003). "A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids". Tetrahedron.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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