Dimethylformamide → 4-(2-Hydroxyethoxy)-3-iodo-5-methoxybenzaldehyde

HRID 1597405Notes

Reaction equation

HRID 1597405 reaction equation
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]N(C=O)C>>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([I:1])[C:3]=1[O:12][CH2:19][CH2:13][OH:16])[CH:7]=[O:8]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 17140644-(2-Hydroxyethoxy)-3-iodo-5-methoxybenzaldehyde

Conditions

Temperature
40 °C

Procedure

5-Iodovanillin (25 g, 90 mmol) in DMF (100 mL) was added to potassium carbonate (18.6 g, 135 mmol). The mixture was heated at 40° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and quenched with water (500 mL) and extracted with ethyl acetate. The organic layer was washed with water and saturated NaCl solution, and dried over MgSO4, filtered and evaporated in vacuo to an oil, and then purified by column chromatography (silica, 2:1 hexane/ethyl acetate), to provide the product (16.6 g 57%). 1H NMR (CDCl3): 2.70 (t, 1H); 3.92 (t, 2H); 3.92 (s, 3H); 3.94 (s, 3H); 4.29 (t, 2H); 7.44 (s, 1H); 7.87 (s, 1H); 9.85 (s, 1H).

Workup

  1. temperatureto cool to room temperature
  2. customquenched with water (500 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil
  8. custompurified by column chromatography (silica, 2:1 hexane/ethyl acetate)
  9. customto provide the product (16.6 g 57%)

Sources & evidence

ORD record
ord-5dd8c8d183db4ccb9df3d8448065ff69
Source dataset
uspto-grants-2001_09
Patent number
US06294574B1

Reaction notes

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