Thionyl Chloride → 4,4-Difluorocyclohexane-1-carbonyl chloride

HRID 433118Notes

Reaction equation

HRID 433118 reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8](O)=[O:9])[CH2:4][CH2:3]1.S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([Cl:14])=[O:9])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27791364,4-Difluorocyclohexanecarboxylic acid

Product 1

HCID 187583104,4-Difluorocyclohexane-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,4-Difluorocyclohexanecarboxylic acid (118.2 g, 0.72 mol) was dissolved in toluene (296 ml). To the clear solution was added thionyl chloride (261 ml, 3.6 mol) and the resultant solution was heated under reflux for 1.5 hours. A sample was taken and concentrated and 1H-NMR indicated complete conversion to the title compound. The reaction was cooled to room temperature and the thionyl chloride was removed under reduced pressure and replaced with toluene to give the title compound as a toluene concentrate at a total volume of 591 ml.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. concentrationconcentrated
  3. customthe thionyl chloride was removed under reduced pressure

Sources & evidence

ORD record
ord-ee4a44f2ed594671823d17e7904d833e
Source dataset
uspto-grants-2003_12
Patent number
US06667314B2

Reaction notes

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