Kolbe–Schmitt reaction

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"Kolbe process" redirects here. For the electrochemical decarboxylation/dimerization reaction, see Kolbe electrolysis.

Kolbe–Schmitt reaction
Named after
Reaction type Addition reaction
Identifiers
Organic Chemistry Portal kolbe-schmitt-reaction
RSC ontology ID RXNO:0000182

The Kolbe–Schmitt reaction or Kolbe process (named after

aromatic hydroxy acid which is also known as salicylic acid (the precursor to aspirin).[2][3][4][5]

The Kolbe–Schmitt reaction
The Kolbe–Schmitt reaction

By using

biocides
used e.g. in personal care products.

The methodology is also used in the industrial synthesis of 3-hydroxy-2-naphthoic acid; the regiochemistry of the carboxylation in this case is sensitive to temperature.[6]

Reaction mechanism

The Kolbe–Schmitt reaction proceeds via the

phenoxide, classically sodium phenoxide (NaOC6H5), to carbon dioxide
to give the salicylate. The final step is the reaction (
anion with an acid
to form the desired salicylic acids (ortho- and para- isomers).

Kolbe–Schmitt reaction
Kolbe–Schmitt reaction

References

  1. doi:10.15227/orgsyn.009.0072
    .
  2. doi:10.1002/jlac.18601130120
    .
  3. doi:10.1002/prac.18850310130
    .
  4. doi:10.1021/cr50016a001
    . (Review)
  5. ISBN 0-205-05838-8
    .
  6. ISBN 3-527-30673-0
    ..

External links

  • [1] Archived 18 October 2020 at the Wayback Machine English Translation of Kolbe's seminal 1860 German article in Annalen der Chemie und Pharmacie that describes the discovery of this reaction. English title: 'On the syntheses of salicylic acid'; German title "Ueber Synthese der Salicylsäure".
  • [2] An animation of the reaction mechanism.
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