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

HRID 2211305Notes

Reaction equation

HRID 2211305 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-methoxybenzaldehydeYield 57%

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) δ2.70 (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)

Sources & evidence

ORD record
ord-acbb1de853594f9ea85181319150b17a
Source dataset
uspto-grants-1995_10
Patent number
US05463083

Reaction notes

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