Methyl iodide → 5-Methoxy-2-nitrobenzaldehyde

HRID 639350Notes

Reaction equation

HRID 639350 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].IC.[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 2303715-Methoxy-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture containing 5-hydroxy-2-nitrobenzaldehyde (1 eq) in DMF with iodomethane (1.1eq) and potassium carbonate (1eq) was stirred at room temperature for 16 hours. The resulting mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried and concentrated to afford 5-methoxy-2-nitrobenzaldehyde in quantitative yield.

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-37213ff9db4e44f194f6df5e6e4fb393
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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