4-Chlorophenol → Methyl(p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863276Notes

Reaction equation

HRID 1863276 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[I-].[K+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CO.C1C=CC=CC=1.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)=[CH:22][CH:21]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531843Methyl(p-chlorophenoxy)[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.19 g of sodium methoxide in 40 ml of methanol is added 3.21 g of 4-chlorophenol. A few crystals of potassium iodide are added, followed by a solution of 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene. The solution is heated at reflux overnight. After cooling to room temperature, the solution is poured into 100 ml of water and extracted with two 100 ml portions of ether. The combined extracts are washed with 50 ml of 5% NaOH, 50 ml of saturated brine and dried over MgSO4. The solvent is evaporated at reduced pressure and the residue is triturated with petroleum ether to give the product as white crystals, mp 100°-101.5° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux overnight
  3. extractionextracted with two 100 ml portions of ether
  4. washThe combined extracts are washed with 50 ml of 5% NaOH, 50 ml of saturated brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated at reduced pressure
  7. customthe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-d6b1ed3de8e347a2b57d8b1705974c2c
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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