Lindgren oxidation

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Lindgren oxidation
Named after Bengt O. Lindgren
Reaction type Organic redox reaction
Identifiers
RSC ontology ID RXNO:0000287

Lindgren oxidation is a selective method for oxidizing aldehydes to carboxylic acids.[1] The reaction is named after Bengt O. Lindgren.

The oxidation takes place in water containing solvent mixtures under slightly acidic conditions (pH 3–5) with sodium chlorite as oxidizer. To avoid complicated oxidation reactions the hypochlorite, which is formed in the reaction, has to be removed from the reaction mixture by scavengers. In the original publication, sulfamic acid and resorcinol were used.[1] George A. Kraus and co-workers were the first to use 2-methyl-2-butene as scavenger under buffered conditions for the oxidation of an aliphatic and an α,β-unsaturated aldehyde.[2][3] Later hydrogen peroxide also proved to work to remove the hypochlorite.[4]

See also[edit]

References[edit]

  1. ^ a b Lindgren, Bengt O.; Nilsson, Torsten (1973). "Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite". Acta Chemica Scandinavica. 27: 888. doi:10.3891/acta.chem.scand.27-0888. 
  2. ^ George A. Kraus; Bruce Roth (1980). "Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system". The Journal of Organic Chemistry. 45 (24): 4825. doi:10.1021/jo01312a004. 
  3. ^ George A. Kraus; Michael J. Taschner (1980). "Model studies for the synthesis of quassinoids. 1. Construction of the BCE ring system". The Journal of Organic Chemistry. 45 (6): 1175. doi:10.1021/jo01294a058. 
  4. ^ Enrico Dalcanale; Fernando Montanari (1986). "Selective oxidation of aldehydes to carboxylic acids with sodium chlorite-hydrogen peroxide". The Journal of Organic Chemistry. 51 (4): 567. doi:10.1021/jo00354a037.