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

HRID 2220989Notes

Reaction equation

HRID 2220989 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-ac795bb4485843339eef8f4889f9c873
Source dataset
uspto-grants-2008_05
Patent number
US07368460B2

Reaction notes

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