Sulfuric Acid → 4-Methylanisole

HRID 848842Notes

Reaction equation

HRID 848842 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1>O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:2])=[CH:10][CH:9]=1.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 1118Sulfuric Acid2×HCID 77314-Methylanisole

Product 2

HCID 77314-MethylanisoleHCID 312444-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Into the same flask as in Example 1 are placed 400 ml of water, 87 g of sulfuric acid, 5 g of manganic sulfate and 100 g of p-methoxytoluene, and the mixture is stirred. Into a 1-liter beaker are placed 540 ml of water, 86 g of chromic anhydride and 246 g of sulfuric acid to prepare an oxidizing solution. The oxidation process of Example 2 is repeated in the same manner except that the reaction temperature is maintained at 80° C for 21/3 hours. The reaction mixture is treated in the same manner as in Example 1, affording 70 g of anisaldehyde, 27 g of unreacted p-methoxytoluene and 5 g of the residue. Conversion 73%. Yield 86%. Aldehyde selectivity 80%.

Workup

  1. customto prepare an oxidizing solution
  2. additionThe reaction mixture is treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-de53053a72e44066b382014d1cb7aeb9
Source dataset
uspto-grants-1981_10
Patent number
US04297520

Reaction notes

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