Sodium Iodide → 2,6-Dichloro-4-(2-methoxyethoxy)benzaldehyde

HRID 1042923Notes

Reaction equation

HRID 1042923 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:20][CH2:21][O:22][C:23](C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:20][CH2:21][O:22][CH3:23])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 866754202,6-Dichloro-4-(2-methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,6-Dichloro-4-hydroxybenzaldehyde (0.5 g, 2.62 mmol), 1-bromo-2-methoxyethone (0.3 mL), sodium iodide (0.4 g, 0.4 mmol) and potassium carbonate (0.9 g, 6.55 mmol) were added in DMF (5 mL) and heated at 100° C. for 1 h under stirring. When the reaction was done, the reaction mixture was diluted with EtOAc and extracted three times with water. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum. The resulting solid was purified by normal phase chromatography (hexanes:EtOAc 3:1) to afford 2,6-dichloro-4-(2-methoxyethoxy)benzaldehyde.

Workup

  1. extractionextracted three times with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum
  5. customThe resulting solid was purified by normal phase chromatography (hexanes:EtOAc 3:1)

Sources & evidence

ORD record
ord-b58495d59c60418d85c4d714b6936c19
Source dataset
uspto-grants-2013_10
Patent number
US08558001B2

Reaction notes

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