The synthesis of amides from amines and esters from alcohols with acyl halides or anhydrides in the presence of a base is known as the Schotten-Baumann reaction. The amine attacks the acyl halide, forming a tetrahedral intermediate that releases a halide ion. Deprotonation of the positively charged nitrogen affords the amide product. Esters are formed from alcohols in a similar fashion.

  • Reagents: Original Conditions: Inorganic Base (NaOH, KOH, Na2CO3, NaHCO3), Water or Modified Conditions: Aprotic Solvent, Organic Base (Pyridine, DMAP, Et3N, etc.) and/or Lewis Acid (MgBr2, Sc(OTf)3, etc.)
  • Reactant: Acyl Halide or Anhydride, 1° or 2° Amine, 1°, 2° or 3° Alcohol
  • Product: Amide or Ester
  • Type of Reaction: Nucleophilic Acyl Substitution


Top Citations

  • Acylation of Nitrogen Heterocycles. II . Carbobenzoxylation of Substituted Adenines under the Conditions of the Schotten-Baumann Reaction. Journal of Heterocyclic Chemistry 1968, 5 (5), 679–682.
  • Development of a Continuous Schotten–Baumann Route to an Acyl Sulfonamide. Org. Process Res. Dev. 2012, 16 (5), 939–957.
  • Release of Hydrogen Cyanide via a Post-Secretion Schotten-Baumann Reaction in Defensive Fluids of Polydesmoid Millipedes. J Chem Ecol. 2011, 37 (3), 232–238.

Related Compounds

  • Base
By shuhan yang


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