4-Chloro-3,5-dimethylphenol → Methyl alpha-(3,5-dimethyl-4-chlorophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1863307Notes

Reaction equation

HRID 1863307 reaction equation
C[O-].[Na+].[I-].[K+].[CH3:6][C:7]1[CH:8]=[C:9]([OH:15])[CH:10]=[C:11]([CH3:14])[C:12]=1[Cl:13].Br[CH:17]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]>CO.C1C=CC=CC=1.O>[CH3:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([CH3:14])[C:12]=1[Cl:13])[O:15][CH:17]([C:22]1[CH:27]=[CH:26][C:25]([O:28][C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

8

Reactant 4

HCID 27234-Chloro-3,5-dimethylphenolHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531855Methyl alpha-(3,5-dimethyl-4-chlorophenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.19 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol is added 3.92 g of 3,5-dimethyl-4-chlorophenol. After one hour, a solution of 7.11 g of methyl α-bromo-α-[p-(p-chlorophenoxy)phenyl]acetate in 10 ml of benzene is added. The solution is refluxed overnight. After cooling to room temperature the mixture is poured into 100 ml of water and extracted with two 60 ml portions of ether. The combined extracts are washed with two 50 ml portions of 5% NaOH, 50 ml of water, 50 ml of saturated brine and dried (MgSO4). Evaporation of the solvent affords a yellow oil which is chromatographed on 100 g silica gel and eluted with 400 ml of benzene. Evaporation of the solvent under vacuum gives the product as a colorless oil.

Workup

  1. temperatureThe solution is refluxed overnight
  2. extractionextracted with two 60 ml portions of ether
  3. washThe combined extracts are washed with two 50 ml portions of 5% NaOH, 50 ml of water, 50 ml of saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customaffords a yellow oil which
  7. customis chromatographed on 100 g silica gel
  8. washeluted with 400 ml of benzene
  9. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-8a770eda6c75473cb38e3eabcf9b244a
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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