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Schotten-Baumann Reaction

April 22, 2013

Schotten-Baumann Reaction involves benzoylation of the compounds having active hydrogen such as phenols, primary amines and secondary amines and alcohols with benzyl chloride under the influence of aqueous NaOH or pyridine. This reaction is named after a German chemist Carl Schotten and Eugen Baumann in 1883.

This reaction is base catalysed and it acts as driving force to shift the equlibrium in the formation of amides from amines and acid chlorides. The base not only to neutralise the HCl formed in the reaction, but also serves to catalyse the reaction. Pyridine in particular seems to convert the acid chloride into even more powerful acylating agent.

Schotten–Baumann reactions

For example, consider the following reaction

Schotten–Baumann reaction

Mechanism of the reaction

  • Amine reacts with acid chloride to form the protonated compound.
  • Base used as a catalyst absorbs the acidic proton which makes the reaction feasible.
  • Once the acidic proton is taken away by the base amide(product)  and hydrochloric acid is formed.

Schotten–Baumann reaction mechanism

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