Thionyl Chloride → 6,6-Difluorohex-5-enoic acid chloride

HRID 963542Notes

Reaction equation

HRID 963542 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:14])=[CH:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12]>CN(C)C=O>[F:5][C:6]([F:14])=[CH:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:3])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 112980566,6-difluorohex-5-enoic Acid

Product 1

HCID 197938396,6-Difluorohex-5-enoic acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.5 ml of thionyl chloride are added dropwise, at room temperature, with stirring, to 7.5 g of 6,6-difluorohex-5-enoic acid and a drop of dimethylformamide. The mixture is then stirred at reflux temperature for 5 hours, the excess thionyl chloride is evaporated off in a rotary evaporator and the residue is distilled at 86° and 100 mbar. The title product is obtained in the form of a colourless fluid.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customthe excess thionyl chloride is evaporated off in a rotary evaporator
  3. distillationthe residue is distilled at 86°

Sources & evidence

ORD record
ord-188ed48966174d8bad9438d9d35af80a
Source dataset
uspto-grants-1998_06
Patent number
US05763481

Reaction notes

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