Iodine → 2-Iodo-4,5-dimethylphenol

HRID 228686

Reaction equation

HRID 228686 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[I:10]I.S([O-])([O-])=O.[Na+].[Na+]>CO.O>[I:10][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=1[OH:9]

Participants

5

Reactant 3

HCID 807IodineHCID 72493,4-DimethylphenolHCID 24437Sodium Sulfite

Product 1

HCID 136352572-Iodo-4,5-dimethylphenolYield 64%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

3,4-Dimethylphenol (0.68 g) and iodine (1.82 g) were dissolved in methanol/water (10 ml/5 ml), and the mixture was stirred at room temperature overnight. An aqueous sodium sulfite solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using ethyl acetate-hexane to give 2-iodo-4,5-dimethylphenol (833 mg, yield 64%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was then washed with water
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3986cdf6743c42169ba8bf3e20a19168
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

Loading…