Method for oxidizing aldehydes to carboxylic acids
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]
^ abLindgren, Bengt O.; Nilsson, Torsten (1973). "Preparation of Carboxylic Acids from Aldehydes (Including Hydroxylated Benzaldehydes) by Oxidation with Chlorite". Acta Chemica Scandinavica. 27: 888–890. doi:10.3891/acta.chem.scand.27-0888.
^George A. Kraus; Bruce Roth (1980). "Synthetic studies toward verrucarol. 2. Synthesis of the AB ring system". The Journal of Organic Chemistry. 45 (24): 4825–4830. doi:10.1021/jo01312a004.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^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): 1175–1176. doi:10.1021/jo01294a058.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^Enrico Dalcanale; Fernando Montanari (1986). "Selective oxidation of aldehydes to carboxylic acids with sodium chlorite-hydrogen peroxide". The Journal of Organic Chemistry. 51 (4): 567–569. doi:10.1021/jo00354a037.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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on 23 October 2023. Retrieved 21 October 2023. "Hem - Astrid Lindgren - Astrid Lindgren". www.astridlindgren.com (in Swedish). Archived from the original...
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family of eicosanoid inflammatory mediators produced in leukocytes by the oxidation of arachidonic acid (AA) and the essential fatty acid eicosapentaenoic...
associations and structural styles. This scheme, proposed by Waldemar Lindgren (1933) classified hydrothermal deposits as follows: Hypothermal — mineral...
PMID 15681804. S2CID 21762775. Oikonen M, Laippala P, Oksaranta O, Lilius EM, Lindgren S, et al. (2003). "Ambient air quality and occurrence of multiple sclerosis...
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Lindgren 1995, p. 310–311. Lindgren 1995, p. 328. Lindgren 1971, p. 117. Lagerlöf 1972, p. 296. Cutler 1969, p. 259. Lindgren 1996, p. 317. Lindgren 1996...
1988. Springer Science & Business Media. p. 717. ISBN 978-3-642-74034-3. Lindgren JE, Holmstedt B (1983). "Guide to the Analysis of Phencyclidine and its...
National Council for Science and the Environment. Giribet, G.; Okusu, A.; Lindgren, A.R.; Huff, S.W.; Schrödl, M.; Nishiguchi, M.K. (May 2006). "Evidence...
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coactivator PGC-1α and stimulates hepatic gluconeogenesis, fatty acid oxidation, and ketogenesis. FGF21 also blocks somatic growth and sensitizes mice...
relatively brief period. The first known mass extinction was the Great Oxidation Event 2.4 billion years ago, which killed most of the planet's obligate...
Archived from the original on 11 November 2017. Retrieved 11 November 2017. Lindgren S (1993). Kliniska färdigheter: Informationsutbytet mellan patient och...
australis Cav". Scientia Pharmaceutica. 53: 169–170. Rivier, Laurent; Lindgren, Jan-Erik (1972). ""Ayahuasca," the South American Hallucinogenic Drink:...
PMC 4603435. PMID 25654408. Axelsson, L. T.; Chung, T. C.; Dobrogosz, W. J.; Lindgren, S. E. (April 1988). "Production of a Broad Spectrum Antimicrobial Substance...
1007/bf00408082. PMID 4559703. S2CID 9204044. Lindas, A.-C.; Karlsson, E. A.; Lindgren, M. T.; Ettema, T. J. G.; Bernander, R. (5 November 2008). "A unique cell...