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

HRID 341847

Reaction equation

HRID 341847 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-dimethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-iodovanillin (7 g, 25.18 mmole), potassium carbonate (8.78 g, 63.53 mmole) and iodomethane (6.43 g, 45.30 mmole) was suspended in 60 mL of DMF and stirred at room temperature for 14 hours. The reaction mixture was quenched with water and extracted with diethyl ether. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to obtain a solid which was recrystallized from hexane/ethyl acetate (2:1) (6.28 g, 85.4%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto obtain a solid which
  7. customwas recrystallized from hexane/ethyl acetate (2:1) (6.28 g, 85.4%)

Sources & evidence

ORD record
ord-cf2a47a2c6ac4469ba02a0f92452f246
Source dataset
uspto-grants-1999_01
Patent number
US05856323

Linked notes

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