Water → 5-Methoxy-2-nitrobenzaldehyde

HRID 1451176Notes

Reaction equation

HRID 1451176 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([CH:17]=1)[CH:15]=[O:16].O>CN(C)C=O>[CH3:3][O:9][C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([CH:17]=1)[CH:15]=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 2303715-Methoxy-2-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (23.34 g, 0.165 mol) and potassium carbonate (22.73 g, 0.165 mol) are added to a solution of 5-hydroxy-2-nitrobenzaldehyde (25 g, 0.149 mol) in N,N-dimethylformamide. The reaction mixture is stirred at room temperature for 18 hours and poured into water. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a brown solid, mp 89°-90° C.

Workup

  1. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0e224b49d3a45feb8406b243c03ea5a
Source dataset
uspto-grants-1997_02
Patent number
US05604180

Reaction notes

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