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Steglich esterification

Chemical reaction

Steglich esterification

Chemical reaction

The Steglich esterification is a variation of an esterification with dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. The reaction was first described by Wolfgang Steglich in 1978. It is an adaptation of an older method for the formation of amides by means of DCC (dicyclohexylcarbodiimide) and 1-hydroxybenzotriazole (HOBT).

:[[File:SteglichVeresterung Uebersicht.svg|center|500px|Steglich overview]]

This reaction generally takes place at room temperature. A variety of polar aprotic solvents can be used. Because the reaction is mild, esters can be obtained that are inaccessible through other methods for instance esters of the sensitive 2,4-dihydroxybenzoic acid. A characteristic is the formal uptake of water generated in the reaction by DCC, forming the urea compound dicyclohexylurea (DCU).

Reaction mechanism

The reaction mechanism is described as follows:

Mechanism Steglich reaction part 1

With amines, the reaction proceeds without problems to the corresponding amides because amines are more nucleophilic. If the esterification is slow, a side-reaction occurs, diminishing the final yield or complicating purification of the product. This side-reaction is a 1,3-rearrangement of the O-acyl intermediate to an N-acylurea which is unable to further react with the alcohol. DMAP suppresses this side reaction, acting as an acyl transfer-reagent in the following manner:

Action of DMAP in the Steglich esterification

References

References

  1. B. Neises, W. Steglich. (1978). "Simple Method for the Esterification of Carboxylic Acids". [[Angew. Chem. Int. Ed.]].
  2. J. C. Sheehan, G. P. Hess. (1955). "A New Method of Forming Peptide Bonds". [[J. Am. Chem. Soc.]].
  3. W. König, R. Geiger. (1970). "Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1-Hydroxy-benzotriazolen". [[Chem. Ber.]].
  4. (2021). "A solvent-reagent selection guide for Steglich-type esterification of carboxylic acids". Green Chem..
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