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

Mechanism

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