The Dakin Reaction allows the preparation of phenols from aryl aldehydes or aryl ketones via oxidation with hydrogen peroxide in the presence of base. The aryl formate or alkanoate formed as an intermediate is subsequently saponified to yield the substituted phenol product.
Ortho or para +M substituents (NH2, OH) favor this reaction.
Mechanism of the Dakin Reaction
See Baeyer-Villiger Oxidation for the oxidation step.
Oxidation of aromatic aldehydes and ketones by H2O2/CH3ReO3 in ionic liquids: a catalytic efficient reaction to achieve dihydric phenols
R. Bernini, A. Coratti, G. Provenzano, G. Fabrizi, D. Tofani, Tetrahedron, 2005, 61, 1821-1825.
The Urea-Hydrogen Peroxide Complex: Solid-State Oxidative Protocols for Hydroxylated Aldehydes and Ketones (Dakin Reaction), Nitriles, Sulfides, and Nitrogen Heterocycles
R. S. Varma, K. P. Naicker, Org. Lett., 1999, 1, 189-191.
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S. Chen, F. W. Foss, Jr, Org. Lett., 2012, 14, 5150-5153.
Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
S. Chen, M. S. Hoassain, F. W. Foss, Jr, Org. Lett., 2012, 14, 2806-2809.