4-Chlorophenol → 2-(2-(4-Chlorophenoxy)phenyl)acetic acid

HRID 1625167Notes

Reaction equation

HRID 1625167 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:23]([OH:25])=[O:24]>[Cu].C1(C)C(C)=CC=CC=1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:23]([OH:25])=[O:24])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 122458712-(2-(4-Chlorophenoxy)phenyl)acetic acidYield 43.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
65 °C

Procedure

xylene (600 mL), potassium carbonate (53.75 g), 4-chlorophenol (46.25 g), and copper powder (2.7 g) are charged in to a round bottom flask at 25-35° C. The reaction mixture heated to 60-70° C., o-chlorophenyl acetic acid (50 g) is added in portions. The reaction mixture is heated to reflux, maintained for 2-3 hours and simultaneously water is removed by azeotropic distillation. The reaction mixture is cooled to below 90° C. Water (600 mL) is added, both layers are separated. The organic layer is washed with water (600 mL). The combined organic layer is cooled to 0-10° C. and conc. HCl (26 mL) is added until the pH reaches to 2.0. The reaction mass is maintained at 0-10° C. for 1 hour, the obtained solid is collected by filtration, washed with water (450 mL), and dried at 60° C. to afford 33.8 g of the title compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained for 2-3 hours
  4. customsimultaneously water is removed by azeotropic distillation
  5. temperatureThe reaction mixture is cooled to below 90° C
  6. additionWater (600 mL) is added
  7. customboth layers are separated
  8. washThe organic layer is washed with water (600 mL)
  9. temperatureThe combined organic layer is cooled to 0-10° C.
  10. additionconc. HCl (26 mL) is added until the pH
  11. temperatureThe reaction mass is maintained at 0-10° C. for 1 hour
  12. filtrationthe obtained solid is collected by filtration
  13. washwashed with water (450 mL)
  14. customdried at 60° C.

Sources & evidence

ORD record
ord-fe917037bd99402e9cc98593cb3aca7e
Source dataset
uspto-grants-2014_07
Patent number
US08779161B2

Reaction notes

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