Kolbe–Schmitt reaction

A chemical reaction used to synthesize salicylic acid

Kolbe–Schmitt reaction

The Kolbe–Schmitt reaction is an important chemical reaction in organic chemistry that involves the carboxylation of phenolates to produce salicylic acid derivatives. This reaction is named after the chemists Hermann Kolbe and Rudolf Schmitt, who developed the process in the late 19th century.

Mechanism of the Kolbe–Schmitt reaction

Mechanism

The Kolbe–Schmitt reaction proceeds through the following steps:

1. Formation of the phenolate ion: The reaction begins with the deprotonation of a phenol to form a phenolate ion. This is typically achieved by treating the phenol with a strong base such as sodium hydroxide (NaOH).
2. Carboxylation: The phenolate ion is then reacted with carbon dioxide (CO₂) under high pressure and elevated temperature. This step results in the formation of a carboxylate intermediate.
3. Protonation: The carboxylate intermediate is then protonated to yield the final product, which is a salicylic acid derivative.

The overall reaction can be summarized as follows:

C₆H₅ONa + CO₂ + H₂O → C₆H₄(OH)COOH + NaOH

Applications

The Kolbe–Schmitt reaction is primarily used in the industrial production of salicylic acid, which is a precursor to aspirin and other pharmaceuticals. Salicylic acid is also used in the manufacture of dyes, preservatives, and as a keratolytic agent in dermatology.

Historical significance

The development of the Kolbe–Schmitt reaction marked a significant advancement in the field of organic synthesis. It provided a practical method for the large-scale production of salicylic acid, which was previously difficult to synthesize efficiently. This reaction laid the groundwork for the development of non-steroidal anti-inflammatory drugs (NSAIDs) and other important medicinal compounds.

Animation of the Kolbe–Schmitt reaction

Related pages

• Salicylic acid
• Aspirin
• Carboxylation
• Phenol
• Hermann Kolbe
• Rudolf Schmitt