Kolbe–Schmitt reaction
| Kolbe–Schmitt reaction | |
|---|---|
| Named after |
Hermann Kolbe Rudolf Schmitt |
| 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 Hermann Kolbe and Rudolf Schmitt) is a carboxylation chemical reaction that proceeds by heating sodium phenoxide (the sodium salt of phenol) with carbon dioxide under pressure (100 atm, 125 °C), then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid (the precursor to aspirin).
By using potassium hydroxide, 4-hydroxybenzoic acid is accessible, an important precursor for the versatile paraben class of biocides used e.g. in personal care products.
The Kolbe–Schmitt reaction proceeds via the nucleophile addition of a phenoxide, classically sodium phenoxide (NaOC6H5), to carbon dioxide to give the salicylate. The final step is reaction of the salicylate with acid to form the desired salicylic acid.
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