Iodine → 2-Iodo-4,5-dimethylphenol
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe mixture was extracted with ethyl acetate
- washThe ethyl acetate layer was then washed with water
- dry with materialwas dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation under the reduced pressure
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-3986cdf6743c42169ba8bf3e20a19168
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Reaction notes
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