Thionyl Chloride → 2-[[4-[4-(Trifluoromethoxy)phenoxy]phenoxy]]propanoyl chloride

HRID 128495Notes

Reaction equation

HRID 128495 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](O)=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.S(Cl)([Cl:27])=O>CN(C=O)C>[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([O:8][C:9]2[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15]([Cl:27])=[O:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23469824HCID 23469824, compound

Product 1

HCID 234698232-[[4-[4-(Trifluoromethoxy)phenoxy]phenoxy]]propanoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 17.11 g. (0.05 mole) of 2-[[4-[4-(trifluoromethoxy)phenoxy]phenoxy]]propanoic acid is added 1 ml. of DMF, followed by 50 ml. of thionyl chloride. After evolution of HCl ceases, the thionyl chloride excess is removed in vacuum. The residue is extracted with methylene chloride and the methylene chloride solution washed with ice water, dried, and the solvent removed, leaving 2-[[4-[4-(trifluoromethoxy)phenoxy]-phenoxy]]propanoyl chloride.

Workup

  1. customAfter evolution of HCl ceases, the thionyl chloride excess is removed in vacuum
  2. extractionThe residue is extracted with methylene chloride
  3. washthe methylene chloride solution washed with ice water
  4. customdried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-f45e87b23fb34b9daf983d84e798b337
Source dataset
uspto-grants-1981_03
Patent number
US04259532

Reaction notes

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