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Dakin Reaction

Lianyungang Klinechem Co.,Ltd | Updated: Dec 05, 2018

Dakin Reaction

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.

Recent Literature

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, Tetrahedron200561, 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.19991, 189-191.

Aerobic Organocatalytic Oxidation of Aryl Aldehydes: Flavin Catalyst Turnover by Hantzsch's Ester
S. Chen, F. W. Foss, Jr, Org. Lett.201214, 5150-5153.

Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
S. Chen, M. S. Hoassain, F. W. Foss, Jr, Org. Lett.201214, 2806-2809.

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