Water → 3-Iodo-4,5-dimethoxybenzaldehyde

HRID 1166754Notes

Reaction equation

HRID 1166754 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)([O-])[O-].[K+].[K+].O>CN(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][CH3:13])[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 27781133-Iodo-4,5-dimethoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

lodomethane (2.5 mL, 40 mmoles) was added to a mixture of 5-iodovanillin (10 g, 36 mmoles), potassium carbonate (25 g, 180 mmoles) in DMF (100 ml) and the resulting mixture was stirred at room temperature for 16 hours. The mixture was poured into water (0.5 L) and extracted with ethyl acetate (2×200 mL). The combined organic phases were washed with water (200 mL), dried over MgSO4 and evaporated in vacuo to afford 9.78 g (93%) of 3,4-dimethoxy-5-iodobenzaldehyde, m.p. 58-63° C.

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phases were washed with water (200 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d69129f06004bbbb6d1fdd285416961
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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