Thionyl Chloride → 2,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

HRID 227367Notes

Reaction equation

HRID 227367 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](O)=[O:8].S(Cl)([Cl:13])=O>>[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([Cl:13])=[O:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acid

Product 1

HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Procedure

To a flask containing 2,2,3,3-tetramethylcyclopropane carboxylic acid (Aldrich, 13.5 g, 95 mmol) was added 30 mL of thionyl chloride (410 mmol, excess). This solution was warmed to reflux and stirred for 2 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The residue was azeotroped three times with 10 mL of benzene to remove any remaining thionyl chloride, and used without further purification.

Workup

  1. temperatureThis solution was warmed
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was azeotroped three times with 10 mL of benzene
  5. customto remove any remaining thionyl chloride
  6. customused without further purification

Sources & evidence

ORD record
ord-018c687564df4805b3824e3c920a7679
Source dataset
uspto-grants-2009_07
Patent number
US07560481B2

Reaction notes

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