Water → 1-Iodo-3,5-dimethoxy-4-(2-methoxyethoxy)benzene

HRID 2181294Notes

Reaction equation

HRID 2181294 reaction equation
[CH3:1]I.[H-].[Na+].[OH:5][CH2:6][CH2:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([I:17])=[CH:11][C:10]=1[O:18][CH3:19].O>O1CCCC1>[I:17][C:12]1[CH:11]=[C:10]([O:18][CH3:19])[C:9]([O:8][CH2:7][CH2:6][O:5][CH3:1])=[C:14]([O:15][CH3:16])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 224856234-(2-Hydroxyethoxy)-1-iodo-3,5-dimethoxybenzene

Product 1

HCID 224855611-Iodo-3,5-dimethoxy-4-(2-methoxyethoxy)benzeneYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (0.010 mL, 0.16 mmol) and a 50% dispersion of sodium hydride in mineral oil (12.0 mg, 0.24 mmol) were added to a solution of 4-(2-hydroxyethoxy)-1-iodo-3,5-dimethoxybenzene (39.0 mg, 0.120 mmol) in anhydrous tetrahydrofuran (1.0 mL), and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with 3.0 M hydrochloric acid, saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-iodo-3,5-dimethoxy-4-(2-methoxyethoxy)benzene as a colorless oil (40.0 mg, yield: 98%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with 3.0 M hydrochloric acid, saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8507621772e74312b958433b90d26bcc
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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