Methyl iodide → 3-Methoxy-4-nitrobenzaldehyde

HRID 509449Notes

Reaction equation

HRID 509449 reaction equation
CI.[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[CH:7]=[O:8].[C:15](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:15][O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 114920433-Methoxy-4-nitrobenzaldehydeYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (55.2 g, 389.2 mmol) was added dropwise to a stirred mixture of 3-hydroxy-4-nitrobenzaldehyde (50 g, 288.4 mmol) and potassium carbonate (53.8 g, 389.2 mmol) in DMF (250 ml). The reaction mixture was stirred overnight, poured into ice-cold water, and the precipitated solid was collected by filtration. The resulting solid was dried on a high vacuum overnight to obtain 53.4 g of 3-methoxy-4-nitrobenzaldehyde.

Workup

  1. additionpoured into ice-cold water
  2. filtrationthe precipitated solid was collected by filtration
  3. customThe resulting solid was dried on a high vacuum overnight

Sources & evidence

ORD record
ord-56011691ac0c44408d3c8df2a4014421
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

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