4-Chlorophenol → HCID 20392611, compound

HRID 1863287Notes

Reaction equation

HRID 1863287 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[I-].[K+].Br[CH:15]([C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1)[C:16]([O:18][CH3:19])=[O:17]>CO.C1C=CC=CC=1.O>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:15]([C:20]2[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 46844-ChlorophenolHCID 4875Potassium IodideHCID 10942334Sodium MethoxideHCID 20392584Methyl α-bromo-4-iodobenzeneacetate

Product 1

HCID 20392611HCID 20392611, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 2.38 g of sodium methylate in 80 ml of methanol is added 6.42 g of 4-chlorophenol and a few crystals of potassium iodide. After 1/2 hour of stirring a solution of 14.2 g of methyl α-bromo-α-(p-iodophenyl)acetate in 6 ml of benzene is added. The mixture is refluxed overnight. After cooling to room temperature, the mixture is added to 200 ml of water and extracted with two 50 ml portions of chloroform. The combined organic layers are washed with 50 ml of 5% NaOH, 50 ml of H2O, 50 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent affords the product as a white solid, mp 122°-125° C. A portion is recrystallized from petroleum ether to yield white crystals, mp 126°-127° C.

Workup

  1. additionis added
  2. temperatureThe mixture is refluxed overnight
  3. extractionextracted with two 50 ml portions of chloroform
  4. washThe combined organic layers are washed with 50 ml of 5% NaOH, 50 ml of H2O, 50 ml of saturated brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dbec92f4e18f4a41a0bb72c07e4eaeef
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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