Methyl iodide → 3-Iodo-4,5-dimethoxybenzaldehyde

HRID 1684037Notes

Reaction equation

HRID 1684037 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+].IC>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 6328Methyl iodideHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 27781133-Iodo-4,5-dimethoxybenzaldehydeYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-iodovanillin (6.0 g, 21.58 mmole), potassium carbonate (5.96 g, 43.16 mmole), iodomethane (9.06 g, 64.77 mmole) and dry DMF (50 ml) were stirred at room temperature under an argon atmosphere overnight. The reaction was quenched with 250 ml H2O and extracted with diethyl ether. The organic layer was dried over MgSO4, and concentrated to an oil in vacuo which was purified by flash column chromatography using 3:1 hexane/ethyl acetate as eluent. The column gives 5.814 g (92%) of a white solid.

Workup

  1. customThe reaction was quenched with 250 ml H2O
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated to an oil in vacuo which
  5. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-d8812581882146a8a353f997c04879d4
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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