Organic reaction developed by William Henry Perkin
Not to be confused with Perkin rearrangement.
Perkin reaction
Named after
William Henry Perkin
Reaction type
Condensation reaction
Reaction
Aromatic aldehyde
+ Aliphatic acid anhydride
+ Alkali salt of the acid
↓
Cinnamic acid derivatives
Identifiers
RSC ontology ID
RXNO:0000003Y
Y(what is this?) (verify)
The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin 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.[1][2] The alkali salt acts as a base catalyst, and other bases can be used instead.[3]
The Perkin reaction
Several reviews have been written.[4][5][6]
^Perkin, W. H. (1868). "On the artificial production of coumarin and formation of its homologues". Journal of the Chemical Society. 21: 53–61. doi:10.1039/js8682100053.
^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. 32: 660–674. doi:10.1039/js8773200660.
^Dippy, J. F. J.; Evans, R. M. (1950). "The nature of the catalyst in the Perkin condensation". J. Org. Chem. 15 (3): 451–456. doi:10.1021/jo01149a001.
^Johnson, J. R. (1942). "The Perkin Reaction and Related Reactions". Org. React. 1: 210–265. doi:10.1002/0471264180.or001.08. ISBN 0471264180.
^House, H. O. (1972) Modern Synthetic Reactions, W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663
^Rosen, T. (1991). "The Perkin Reaction". Compr. Org. Synth. 2: 395–408. doi:10.1016/B978-0-08-052349-1.00034-2. ISBN 978-0-08-052349-1.
The Perkinreaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated...
Sir William Henry Perkin FRS (12 March 1838 – 14 July 1907) was a British chemist and entrepreneur best known for his serendipitous discovery of the first...
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hydrogen compound is sufficiently activated the reaction is called a Knoevenagel condensation. In a Perkinreaction the aldehyde is aromatic and the enolate...
In organic chemistry, the Perkin rearrangement (coumarin–benzofuran ring contraction) is a rearrangement reaction in which a 2-halocoumarin in the presence...
Royale in 1882. Coumarin can be prepared by a number of name reactions, with the Perkinreaction between salicylaldehyde and acetic anhydride being a popular...
electrophilic attack of the arene. Aldol condensation Kostanecki acylation Perkinreaction J. A. Joule, K. Mills Heterocyclic Chemistry, 4th edition, Blackwell...
subsequent decarboxylation leads to 4. {Alternatively it can be formed by Perkinreaction between p-fluorobenzaldehyde and propionic anhydride in the presence...
resulting ether and decarboxylation. Perkin rearrangement, where a coumarin is reacted with a hydroxide: Diels–Alder reaction[clarification needed] of nitro...
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dihalide. This reaction is also called the Perkin alicyclic synthesis (see: alicyclic compound) after investigator William Henry Perkin, Jr. In the manufacture...
Anthony 'Tony' Perkins (April 4, 1932 – September 12, 1992) was an American actor, director, and singer. He is most notable for the role of Norman Bates...
the first synthetic perfumes, and cinnamic acid via the Perkinreaction – William Henry Perkin Dew Point Hygrometer – John Frederic Daniell Earnshaw's...
trifluoromethanesulphonate salts and their reactions with some oxygen and sulphur nucleophiles". Journal of the Chemical Society, Perkin Transactions 1: 1067–1073. doi:10...
Smith, L. C. (1979). "The mechanism of the barton reaction". Journal of the Chemical Society, Perkin Transactions 1: 1159. doi:10.1039/P19790001159. hdl:1893/35137...
this issue. Compared to the Wittig, Wittig-Horner, Perkin, or transition-metal-catalyzed reactions to synthesize pterostilebene, the Julia olefination...
The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine...
In organic chemistry, the Mallory reaction is a photochemical-cyclization–elimination reaction of diaryl-ethylene structures to form phenanthrenes and...
the first synthetic perfumes), and cinnamic acid via the Perkinreaction by William Henry Perkin (1838–1907). 1893: The Weston cell developed by England-born...
"Mechanistic studies on the reaction of nitro- and nitrosoarenes with vinyl Grignard reagents". Journal of the Chemical Society, Perkin Transactions 2. 1991...
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