Potassium Iodide → Methyl alpha-(3,5-di-tert-butylphenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

HRID 1704058Notes

Reaction equation

HRID 1704058 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[I-].[K+].Br[CH:22]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=2)=[CH:29][CH:28]=1)[C:23]([O:25][CH3:26])=[O:24]>CO.C1C=CC=CC=1>[C:11]([C:9]1[CH:8]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)[O:15][CH:22]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=2)=[CH:29][CH:28]=1)[C:23]([O:25][CH3:26])=[O:24])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 708253,5-Di-tert-butylphenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531858Methyl alpha-(3,5-di-tert-butylphenoxy)-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 5.16 g of 3,5-di-tert-butylphenol, 1.188 g of sodium methoxide, and 50 mg of potassium iodide in 40 ml of methanol is added 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 and worked up as described in Example 70 to yield a yellow oil which is purified by chromatography on 100 g of silica gel (benzene, 400 ml) and pumped in vacuo at 120° C (0.05 mm) to yield a yellow glass.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux overnight
  3. customto yield a yellow oil which
  4. customis purified by chromatography on 100 g of silica gel (benzene, 400 ml)
  5. custompumped in vacuo at 120° C
  6. customto yield a yellow glass

Sources & evidence

ORD record
ord-fafba5f4c8604c659a5829c942266be7
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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