Thionyl Chloride → 4-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chloride

HRID 973186Notes

Reaction equation

HRID 973186 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:26])([F:25])[C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][CH:11]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:12](O)=[O:13]>C(Cl)(Cl)Cl>[F:5][C:6]([F:26])([F:25])[C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][CH:24]=1)[O:10][CH:11]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[C:12]([Cl:3])=[O:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 99494114687-08-5

Product 1

HCID 121092354-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chlorideYield 100.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (44.5 g., 0.375 mole) is added over a five-minute period to a suspension of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetic acid (100 g., 0.30 mole) in 125 ml. of chloroform. The mixture is stirred at room temperature for 30 minutes and then heated under reflux for six hours. As soon as the temperature reaches the boiling point a clear homogenous solution results. At the end of the reaction period, the solvent and volatile reaction products are removed by evaporation in vacuo. High purity (3-trifluoromethylphenoxy)(4-chlorophenyl)acetyl chloride (105 g.) is obtained as a residual oil in almost theoretical yield.

Workup

  1. temperatureheated
  2. temperatureunder reflux for six hours
  3. customresults
  4. customAt the end of the reaction period
  5. customthe solvent and volatile reaction products are removed by evaporation in vacuo

Sources & evidence

ORD record
ord-fee50b8de9d54389aecd866b6b98f013
Source dataset
uspto-grants-1977_10
Patent number
US04055592

Reaction notes

Loading…