Dimethyl Sulfoxide → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

HRID 904590Notes

Reaction equation

HRID 904590 reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1Cl.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].[OH2:23]>>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1[O:23][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][CH:7]=1)[C:17]([OH:18])=[O:20]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 94813,4-DichlorobenzotrifluorideHCID 11430Potassium Carbonate

Product 1

HCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acidYield 85%

Procedure

To a 300 ml. 3-necked flask fitted with a magnetic stirring bar, condenser, drying tube and thermometer is charged the solid from above dimethylsulfoxide (100 ml), 3,4-dichlorobenzotrifluoride (21.5 g. 0.10 mole) and anhydrous potassium carbonate (5.0 g) to assure an alkaline pH. The reaction temperature is taken rapidly to 138°-44° C. while vigorous stirring is maintained. After 4 hours a significant conversion is realized and heating is continued overnight (total 22 hrs.). The reaction mixture is then cooled to room temperature and poured into water (1000 ml) and the aqueous reaction mixture extracted with CCl4 (200 ml). The aqueous layer is then decanted and acidified to pHl with concentrated hydrochloric acid. The white solid that precipitated is collected by filtration and vacuum dried at 60° C. overnight to give 27 g of an off-white solid 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (85% yield), mp 124°-5° C.

Workup

  1. custom3-necked flask fitted with a magnetic stirring bar, condenser
  2. customdrying tube
  3. customis taken rapidly to 138°-44° C.
  4. temperatureis maintained
  5. temperatureheating
  6. waitis continued overnight
  7. custom(total 22 hrs.)
  8. extractionthe aqueous reaction mixture extracted with CCl4 (200 ml)
  9. customThe aqueous layer is then decanted
  10. customThe white solid that precipitated
  11. filtrationis collected by filtration and vacuum
  12. customdried at 60° C. overnight

Sources & evidence

ORD record
ord-18bf58c064734086af7208d159d1485c
Source dataset
uspto-grants-1983_12
Patent number
USRE031455

Reaction notes

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