4-Methylanisole → 4-Methoxybenzaldehyde

HRID 1759284Notes

Reaction equation

HRID 1759284 reaction equation
[N+]([O-])([O-])=O.[Ce+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=[O:15].[NH4+].[Ce].[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>CO>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH:20]=[O:15])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 77314-MethylanisoleHCID 22985Ammonium nitrateHCID 23974CeriumHCID 24948Cerium nitrate

Product 1

HCID 312444-MethoxybenzaldehydeYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol solution of 24.6 g of cerium(III) nitrate is placed into an anode chamber, and a methanol solution of 2 g of ammonium nitrate is placed into a cathode chamber. The cerium salt is electrolyzed with a constant current of 50 mA to pass electricity across the electrodes in a quantity of 1.2 F/mole. A 1.22 g quantity of p-methyl anisole is added to the solution withdrawn from the anode chamber after the electrolysis, and the mixture is stirred for 30 minutes. The same procedure as in Example 1 is thereafter repeated, giving 1.312 g of anisaldehyde. Yield: 96.5%.

Workup

  1. customwithdrawn from the anode chamber after the electrolysis

Sources & evidence

ORD record
ord-4de6f2ca5b30486fbfc0acf90b485ec3
Source dataset
uspto-grants-1982_07
Patent number
US04339607

Reaction notes

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