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.[7]
Applications
Benzaldehyde reacts with acetic anhydride in the presence of sodium or potassium acetate to form cinnamic acid.
^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. ISBN0471264180.
^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. ISBN978-0-08-052349-1.
^Bansal, Raj K. (1998) Organic Reaction Mechanisms, Tata McGraw Hill, 3rd Edition , pp. 199–201, ISBN9780470858585doi:10.1002/0470858583.
^Solladié, Guy; Pasturel-Jacopé, Yacine; Maignan, Jean (2003). "A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids". Tetrahedron. 59 (18): 3315–3321. doi:10.1016/S0040-4020(03)00405-8. ISSN 0040-4020.
February 24, 2023
perkin, reaction, confused, with, perkin, rearrangement, organic, reaction, developed, english, chemist, william, henry, perkin, that, used, make, cinnamic, acids, gives, unsaturated, aromatic, acid, substituted, aryl, acrylic, acid, aldol, condensation, aroma. Not to be confused with Perkin rearrangement The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids It gives an a b unsaturated aromatic acid or a substituted b 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 Perkin reactionNamed after William Henry PerkinReaction type Condensation reactionReactionAromatic aldehyde Aliphatic acid anhydride Alkali salt of the acid Cinnamic acid derivativesIdentifiersRSC ontology ID RXNO 0000003 Y Y what is this verify Several reviews have been written 4 5 6 Contents 1 Reaction mechanism 2 Applications 3 See also 4 ReferencesReaction mechanism Edit Clear from the reaction mechanism the anhydride of aliphatic acid must contain at least 2 a H for the reaction to occur The above mechanism is not universally accepted as several other versions exist including decarboxylation without acetic group transfer 7 Applications EditBenzaldehyde reacts with acetic anhydride in the presence of sodium or potassium acetate to form cinnamic acid One notable application for the Perkin reaction is in the laboratory synthesis of the phytoestrogenic stilbene resveratrol c f fo ti 8 See also EditErlenmeyer Plochl azlactone and amino acid synthesis Stobbe condensation Pechmann condensationReferences Edit 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 Bansal Raj K 1998 Organic Reaction Mechanisms Tata McGraw Hill 3rd Edition pp 199 201 ISBN 9780470858585 doi 10 1002 0470858583 Solladie Guy Pasturel Jacope Yacine Maignan Jean 2003 A re investigation of resveratrol synthesis by Perkins reaction Application to the synthesis of aryl cinnamic acids Tetrahedron 59 18 3315 3321 doi 10 1016 S0040 4020 03 00405 8 ISSN 0040 4020 Retrieved from https en wikipedia org w index php title Perkin reaction amp oldid 1139139452, wikipedia, wiki, book, books, library,
