Potassium Iodide → HCID 12531845, compound

HRID 1863296Notes

Reaction equation

HRID 1863296 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[I-].[K+].Br[CH:18]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1)[C:19]([O:21][CH3:22])=[O:20]>CO.C1C=CC=CC=1.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:18]([C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[CH:25][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 73934-tert-ButylphenolHCID 10942334Sodium MethoxideHCID 20392594Methyl alpha-Bromo-alpha-[p-(p-chlorophenoxy)phenyl]acetate

Product 1

HCID 12531845HCID 12531845, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.75 g of 4-tert-butylphenol and 1.19 g of sodium methoxide and a few crystals 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 mixture is refluxed overnight. On cooling, a white solid separates. The entire mixture is poured into 100 ml of water and extracted with two 100 ml portions of ether. The combined extracts are washed with 100 ml of 5% NaOH, 100 ml of water and saturated brine, and dried over MgSO4. Evaporation of the solvent affords a white solid, which is crystallized from hexane to give the product as fine white needles, mp 118°-120° C.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. temperatureOn cooling
  3. extractionextracted with two 100 ml portions of ether
  4. washThe combined extracts are washed with 100 ml of 5% NaOH, 100 ml of water and saturated brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. customaffords a white solid, which
  8. customis crystallized from hexane

Sources & evidence

ORD record
ord-6b416c899df149dea3332fc355d3f910
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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