Potassium Carbonate → 3-Methoxy-4-nitrobenzaldehyde

HRID 1854654Notes

Reaction equation

HRID 1854654 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6].[C:13](=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[CH3:13][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 114920433-Methoxy-4-nitrobenzaldehydeYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Hydroxy-4-nitrobenzaldehyde (500 mg, 2.99 mmol) and potassium carbonate (0.42 g, 3.0 mmol) were dissolved in 6.0 mL of N,N-dimethylormamide. After addition of iodemethane (0.38 mL, 6.0 mmol) at room temperature, the mixture was stirred for 5 h at the same temperature. The reaction mixture was diluted with ethyl acetate and water, and separated. The organic layer was washed with brine twice, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1) to obtain the title compound as a pale yellow powder (518 mg, 96%).

Workup

  1. additionAfter addition of iodemethane (0.38 mL, 6.0 mmol) at room temperature
  2. customseparated
  3. washThe organic layer was washed with brine twice
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record
ord-4976342f17db4a47bfdc65cd5d743694
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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