Sodium Iodide → 2-Benzyl-4-iodophenol

HRID 2216348

Reaction equation

HRID 2216348 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:15].[Na+].[OH-].[Na+].Cl[O-].[Na+]>O.CO>[CH2:1]([C:8]1[CH:13]=[C:12]([I:15])[CH:11]=[CH:10][C:9]=1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 242162-BenzylphenolHCID 23665760Sodium Hypochlorite

Product 1

HCID 219422992-Benzyl-4-iodophenolYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

6.87 g of 2-benzylphenol, 7.2 g of sodium iodide and 1.7 g of sodium hydroxide were added to 60 ml of methanol and while stirring in an ice bath, 50 ml of an aqueous 5% sodiumhypochlorite solution was added dropwise to the mixture over 30 minutes. The temperature was slowly returned to room temperature and the stirring was continued overnight. Water was added to the reaction mixture, which then was extracted with ethyl acetate, washed with brine and then dried over anhydrous magnesium sulfate. The solvent was removed and the residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give 10.1 g of the title compound.

Workup

  1. customwas slowly returned to room temperature
  2. extractionthen was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8a37bc6ebaf4cc9b95f83e5e3f45a8e
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Linked notes

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