Benzene → Methyl(m-tert.-butylphenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate

HRID 1704111Notes

Reaction equation

HRID 1704111 reaction equation
Br[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:25]([C:29]1[CH:30]=[C:31]([OH:35])[CH:32]=[CH:33][CH:34]=1)([CH3:28])([CH3:27])[CH3:26].C1C=CC=CC=1.C[O-].[Na+]>[I-].[K+].CO>[CH3:6][O:5][C:3](=[O:4])[CH:2]([O:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:30]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 10942334Sodium MethoxideHCID 22761172HCID 22761172, compound

Product 1

HCID 131711337Methyl(m-tert.-butylphenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetateYield 48.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 8.27 g of methyl bromo{p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate, 3.75 g of m-tert.-butylphenol, 10 ml of benzene and 40 ml of methanol is added 1.19 g of sodium methoxide and 50 mg of potassium iodide. The mixture is refluxed for 24 hours and the solvent removed under reduced pressure. To the residue is added acetone and hexane and the mixture is filtered. The filtrate is dried (MgSO4) and concentrated under reduced pressure to give an oil. The oil is chromatographed over silica gel with dichloromethane as eluent to give 4.72 g of product as a colorless viscous oil.

Workup

  1. temperatureThe mixture is refluxed for 24 hours
  2. customthe solvent removed under reduced pressure
  3. additionTo the residue is added acetone and hexane
  4. filtrationthe mixture is filtered
  5. dry with materialThe filtrate is dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil
  8. customThe oil is chromatographed over silica gel with dichloromethane as eluent

Sources & evidence

ORD record
ord-a0a3d0f33cc244d783f3d92614b3d5c4
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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