Module 5 : Reactions with Miscellaneous Reagents

Lecture 37 : N,N-Dicyclohexylcarbodiimide (DCC)

 

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5.2.2 Synthesis of Esters

The synthesis of esters from carboxylic acids and alcohols can be accomplished in the presence of DCC in CH2 Cl2 solvent at ambient conditions. This reaction is called Steglich esterification and usually for the sterically hindered substrates (Scheme 4).

Scheme 4

Mechanism

The carboxylic acid proceeds reaction with DCC to afford activated acylating agent that undergoes reaction with the alcohol (Scheme 5).

Scheme 5

5.2.3 Synthesis of Ethers and Thioethers

Phenols and thiophenols can be reacted with alcohols to give ethers in the presence of DCC (Scheme 5).

Scheme 6