Rearrangement reaction of a phenolic ester to a keto-substituted phenol
Fries rearrangement
Named after
Karl Theophil Fries
Reaction type
Rearrangement reaction
Identifiers
Organic Chemistry Portal
fries-rearrangement
RSC ontology ID
RXNO:0000444
The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenolic ester to a hydroxy aryl ketone by catalysis of Lewis acids.[1][2][3][4]
It involves migration of an acyl group of phenol ester to the aryl ring. The reaction is ortho and para selective and one of the two products can be favoured by changing reaction conditions, such as temperature and solvent.
^Fries, K.; Finck, G. (1908). "Über Homologe des Cumaranons und ihre Abkömmlinge". Chemische Berichte. 41 (3): 4271–4284. doi:10.1002/cber.190804103146.
^Fries, K.; Pfaffendorf, W. (1910). "Über ein Kondensationsprodukt des Cumaranons und seine Umwandlung in Oxindirubin". Chemische Berichte. 43 (1): 212–219. doi:10.1002/cber.19100430131.
^March, J. Advanced Organic Chemistry, 3rd Ed.; John Wiley & Sons: Chichester, 1985; S. 499ff.
^Blatt, A. H. Org. React.1942, 1.
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W X Y Z See also External links 1,2-Wittig rearrangement 1,3-Dipolar cycloaddition 2,3-Wittig rearrangement Abramovitch–Shapiro tryptamine synthesis Acetalisation...
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umami taste in fried onions and coffee roasting. It contributes to the darkened crust of baked goods, the golden-brown color of French fries and other crisps...
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