Potassium Iodide → HCID 12531845, compound

HRID 1704038Notes

Reaction equation

HRID 1704038 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 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 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-1449e4d236354151ad42acd0d93b3c2e
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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