Water → (p-Chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetic acid

HRID 1863320Notes

Reaction equation

HRID 1863320 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([O:8][CH:9]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:10]([O:12]C)=[O:11])=[CH:6][CH:5]=1.O>CO>[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([O:8][CH:9]([C:14]2[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:18][CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 12531843Methyl(p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531874(p-Chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetic acidYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10 g of KOH in 80 ml of 50% methanol is added 30.2 g of methyl (p-chlorophenoxy)-[p-(p-chlorophenoxy)phenyl]acetate. The mixture is refluxed for 3 hours, cooled, poured into 100 ml of water. The solution is extracted with two 100-ml portions of ether. The aqueous layer is acidified with concentrated hydrochloric acid. The mixture is extracted with two 100-ml portions of ether and the extracts are washed with water, brine and dried (MgSO4). Evaporation of the solvent yields an oil which is triturated with petroleum ether to give 27.5 g of product as white crystals. Recrystallization from hexane-chloroform gives white plates, mp 141°-142° C.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. temperaturecooled
  3. extractionThe solution is extracted with two 100-ml portions of ether
  4. extractionThe mixture is extracted with two 100-ml portions of ether
  5. washthe extracts are washed with water, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customyields an oil which
  9. customis triturated with petroleum ether

Sources & evidence

ORD record
ord-facb2020291140a78b889f480399fdf3
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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