| Revision as of 08:42, 5 February 2010 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{reactionbox}} (changes to verified fields) for Misplaced Pages:WikiProject_Chemistry (report errors or bugs)← Previous edit | Latest revision as of 15:18, 14 November 2024 edit undo5.178.188.143 (talk)No edit summaryTag: Visual edit | ||
| (69 intermediate revisions by 51 users not shown) | |||
| Line 1: | Line 1: | ||
| {{Short description|Organic reaction developed by William Henry Perkin}} | |||
| {{distinguish|Perkin rearrangement}} | |||
| {{Use dmy dates|date=January 2024}} | |||
| {{Reactionbox | {{Reactionbox | ||
| ⚫ | |verifiedrevid = 342064841 | ||
| | Verifiedfields = changed | |||
| ⚫ | |Type = Condensation reaction | ||
| ⚫ | | |
||
| ⚫ | |NamedAfter = ] | ||
| ⚫ | | |
||
| ⚫ | |Section2 = {{Reactionbox Identifiers | ||
| ⚫ | | |
||
| ⚫ | |RSC_ontology_id_verified = rsccite | ||
| ⚫ | | |
||
| ⚫ | |RSC_ontology_id = 0000003 | ||
| ⚫ | |||
| ⚫ | | |
||
| ⚫ | |||
| ⚫ | | |
||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| ⚫ | |||
| }} | }} | ||
| ⚫ | |Reaction = {{Reactionbox Reaction | ||
| The '''Perkin reaction''' is an ] developed by ] that can be used to make ]s by the ] of ] ] and ]s in the presence of an alkali salt of the acid.<ref>Perkin, W. H.; '']'' '''1868''', ''21'', 53, 181.</ref><ref>Perkin, W. H.; '']'' '''1877''', ''31'', 388.</ref> | |||
| ⚫ | |Reactant1 = ] ] | ||
| ⚫ | |Reactant2 = ] | ||
| ⚫ | |Reagent1 = ] salt of the ] | ||
| ⚫ | |Product1 = ] derivatives | ||
| ⚫ | }} | ||
| ⚫ | }} | ||
| The '''Perkin reaction''' is an ] developed by ] ] ] in 1868 that is used to make ]s. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the ] of an ] ] and an ], in the presence of an alkali salt of the acid.<ref>{{cite journal|author=Perkin, W. H.|journal=Journal of the Chemical Society|year=1868|volume=21|pages= 53–61|doi=10.1039/js8682100053|title= On the artificial production of coumarin and formation of its homologues|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817479;view=1up;seq=65}}</ref><ref>{{cite journal|author=Perkin, W. H.|journal=Journal of the Chemical Society|year=1877|volume=32|pages= 660–674|doi=10.1039/js8773200660|title= On some hydrocarbons obtained from the homologues of cinnamic acid; and on anethol and its homologues|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015077817446;view=1up;seq=1444}}</ref> The alkali salt acts as a ] ], and other bases can be used instead.<ref>{{cite journal |title= The nature of the catalyst in the Perkin condensation |first1= J. F. J. |last1= Dippy |first2= R. M. |last2= Evans |journal= J. Org. Chem. |year= 1950 |volume= 15 |issue= 3 |pages= 451–456 |doi= 10.1021/jo01149a001}}</ref> | |||
| ] | ] | ||
| Several reviews have been written.<ref>Johnson, J. R. |
Several reviews have been written.<ref>{{cite journal|author=Johnson, J. R.|journal=Org. React.|year=1942|volume=1|pages= 210–265|doi=10.1002/0471264180.or001.08|title=The Perkin Reaction and Related Reactions|isbn=0471264180}}</ref><ref>House, H. O. (1972) ''Modern Synthetic Reactions'', W. A. Benjamin, Menlo Park, California, 2nd ed, pp. 660–663</ref><ref>{{cite journal|author=Rosen, T.|journal=Compr. Org. Synth.|year=1991|volume=2|pages= 395–408|doi=10.1016/B978-0-08-052349-1.00034-2|title=The Perkin Reaction|isbn=978-0-08-052349-1}}</ref> | ||
| ⚫ | ==Reaction mechanism== | ||
| ⚫ | ] | ||
| 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.<ref>Bansal, Raj K. (1998) ''Organic Reaction Mechanisms'', Tata McGraw Hill, 3rd Edition , pp. 199–201, {{ISBN|9780470858585}} {{doi|10.1002/0470858583}}.</ref> | |||
| ⚫ | ==Reaction mechanism== | ||
| ⚫ | ] | ||
| ==Applications== | |||
| The above mechanism is not universally accepted, as several versions exist, including decarboxylation without acetic group transfer {{Fact|date=November 2007}}. | |||
| * Salicylaldehyde converted to ] using acetic anhydride with acetate as base.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.t11_t02 |chapter=Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2016 |last1=Panten |first1=Johannes |last2=Surburg |first2=Horst |pages=1–45 |isbn=978-3-527-30673-2 }}</ref> | |||
| * cinnamic acid is prepared from ], again using acetic anhydride in the presence of sodium or potassium acetate. | |||
| * ] (c.f. ]), a ] ] is yet another product of this methodology.<ref name="SolladiéPasturel-Jacopé2003">{{cite journal|last1=Solladié|first1=Guy|last2=Pasturel-Jacopé|first2=Yacine|last3=Maignan|first3=Jean|title=A re-investigation of resveratrol synthesis by Perkins reaction. Application to the synthesis of aryl cinnamic acids|journal=Tetrahedron|volume=59|issue=18|year=2003|pages=3315–3321|issn=0040-4020|doi=10.1016/S0040-4020(03)00405-8}}</ref> | |||
| ⚫ | ==See also== | ||
| ⚫ | *] | ||
| ⚫ | *] | ||
| *] | |||
| ==References== | ==References== | ||
| {{reflist}} | {{reflist}} | ||
| ⚫ | ==See also== | ||
| ⚫ | *] | ||
| ⚫ | *] | ||
| {{DEFAULTSORT:Perkin Reaction}} | |||
| ] | ] | ||
| ] | ] | ||
| {{sci-stub}} | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
| ] | |||
Latest revision as of 15:18, 14 November 2024
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 | |||||||||||
| |||||||||||
| Identifiers | |||||||||||
| RSC ontology ID | RXNO:0000003 | ||||||||||
 Y(what is this?) (verify) | |||||||||||
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.
Several reviews have been written.
Reaction mechanism
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 (c.f. fo-ti), a phytoestrogenic stilbene is yet another product of this methodology.
See also
References
- 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.
- Panten, Johannes; Surburg, Horst (2016). "Flavors and Fragrances, 3. Aromatic and Heterocyclic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–45. doi:10.1002/14356007.t11_t02. ISBN 978-3-527-30673-2.
- 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.