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Swern Oxidation

Swern Oxidation (Oxidation.) Converts CCO to CC=O using (COCl)₂ (oxalyl chloride), DMSO, Et₃N. Conditions: -78°C.

Oxidation

Reaction details

Name

Swern Oxidation

Type

Oxidation

Starting Material

CCO

Product

CC=O

Reagents
  • (COCl)₂ (oxalyl chloride)

  • DMSO

  • Et₃N

Conditions

-78°C

Mechanism
  1. Smiles

    CCO

    Description

    Primary alcohol

  2. Smiles

    CC=O

    Description

    Aldehyde (no over-oxidation)

Tips
  1. No heavy metals (unlike PCC, Jones)

  2. Very mild conditions

  3. Stops at aldehyde

  4. Bad smell from DMSO byproduct

Related Reactions
  • pcc-oxidation

  • dess-martin-oxidation

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