Methyl iodide → 5-Methoxy-2-nitrobenzaldehyde

HRID 2117647Notes

Reaction equation

HRID 2117647 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].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.C(OCC)(=O)C>[CH3:13][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

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 2303715-Methoxy-2-nitrobenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-hydroxy-2-nitro-benzaldehyde (10 g, 59.8 mmol) and cesium carbonate (23 g, 70.6 mmol) in DMF (40 mL) was added iodomethane (8.8 mL, 141 mmol), and the mixture stirred at room temperature for 17 h. The resulting red-orange suspension was diluted with ethyl acetate and the mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford a thick yellow oil which solidified on standing to afford 5-methoxy-2-nitro-benzaldehyde.

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a thick yellow oil which

Sources & evidence

ORD record
ord-473f7179d21044e38c07473784bf4a58
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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