Sulfuric Acid → 4-Methylanisole

HRID 848841Notes

Reaction equation

HRID 848841 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
35 °C

Procedure

Into the same flask as in Example 1 are placed 400 ml of water, 86 g of sulfuric acid and 100 g of p-methoxytoluene, and the mixture is stirred. A 540 ml quantity of water, 54 g of chromic anhydride and 200 g of sulfuric acid are placed in a 1-liter beaker to prepare an oxidizing solution. The solution is slowly added dropwise to the mixture in the flask with stirring while maintaining the reaction temperature constantly at 35° C. After the whole solution has been added, the mixture is stirred for further 20 minutes. The total reaction time is 5 hours and a half. The reaction mixture is treated and distilled to fractions in the same manner as in Example 1, giving 32 g of anisaldehyde and 60 g of recovered unreacted p-methoxytoluene.

Workup

  1. customto prepare an oxidizing solution
  2. additionThe solution is slowly added dropwise to the mixture in the flask
  3. stirringwith stirring
  4. additionAfter the whole solution has been added
  5. stirringthe mixture is stirred for further 20 minutes
  6. additionThe reaction mixture is treated
  7. distillationdistilled to fractions in the same manner as in Example 1

Sources & evidence

ORD record
ord-ae7e952a491c426683ef480d8ce70600
Source dataset
uspto-grants-1981_10
Patent number
US04297520

Reaction notes

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