4-Methylanisole → 4-Methoxybenzaldehyde

HRID 1759280Notes

Reaction equation

HRID 1759280 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N+]([O-])([O-])=[O:11].[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]=[O:11])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 77314-MethylanisoleHCID 9869224Ammonium cerium (IV) nitrate

Product 1

HCID 312444-MethoxybenzaldehydeYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1.22 g quantity of p-methyl anisole and 23.0 g of ammonium cerium(IV) nitrate are placed into a reactor, and 100 ml of methanol is further placed into the reactor. The mixture is stirred at room temperature for about 30 minutes. After the completion of the reaction, the methanol is distilled off from the reaction mixture. The residue is diluted with water and then subjected to extraction with benzene three times. The extract is washed with an aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue is distilled in a vacuum, giving 1.308 g of anisaldehyde (b.p. 90°-92° C./2 mm Hg). Yield: 96.2%.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe methanol is distilled off from the reaction mixture
  3. additionThe residue is diluted with water
  4. extractionsubjected to extraction with benzene three times
  5. washThe extract is washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled
  8. customto remove the solvent
  9. distillationThe residue is distilled in a vacuum

Sources & evidence

ORD record
ord-4cfacf3dacc34f9dae1f2278d9a6b8cb
Source dataset
uspto-grants-1982_07
Patent number
US04339607

Reaction notes

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