Hydrochloric Acid → 4-Ethoxy-1-iodo-3,5-dimethoxybenzene

HRID 2181289Notes

Reaction equation

HRID 2181289 reaction equation
[I:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH2:13](I)[CH3:14].[H-].[Na+].Cl>CN(C)C=O>[CH2:13]([O:10][C:5]1[C:4]([O:11][CH3:12])=[CH:3][C:2]([I:1])=[CH:7][C:6]=1[O:8][CH3:9])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 224855374-Iodo-2,6-dimethoxyphenol

Product 1

HCID 224855594-Ethoxy-1-iodo-3,5-dimethoxybenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-2,6-dimethoxyphenol (JP61-207432A) (100.0 mg, 0.360 mmol) in dimethylformamide (1.0 mL) were added ethyl iodide (84.0 mg, 0.540 mmol) and a 50% dispersion of sodium hydride in mineral oil (19.0 mg, 0.40 mmol). After stirring at room temperature for 1 hour, the reaction mixture was poured into 0.10 M hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to afford 4-ethoxy-1-iodo-3,5-dimethoxybenzene as a colorless amorphous powder (102.0 mg, yield: 93%).

Workup

  1. extractionthe resulting mixture was extracted with diethyl ether
  2. washThe organic layer was washed with 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-a16ac753536e4c9bbfbfecf08bda3f2d
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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