Hydrogen Peroxide → 4-Methoxybenzaldehyde

HRID 1918438Notes

Reaction equation

HRID 1918438 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.OO.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[O-][W]([O-])(=O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+].P([O-])([O-])(O)=O.[Na+].[Na+].C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[O:8])=[CH:9][CH:10]=1

Participants

9

Reactant 3

HCID 784Hydrogen PeroxideHCID 77384-Methoxybenzyl alcoholHCID 14798Sodium Hydroxide

Product 1

HCID 312444-MethoxybenzaldehydeYield 86.9%

Reagents, catalysts & solvents 5

HCID 24203Sodium Phosphate, DibasicCatalystHCID 26052Sodium tungstateCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 23672064Monosodium phosphateCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
94.5 °C

Procedure

In a glass-made reaction vessel equipped with a thermometer, a temperature controller, a dropping device and a stirring device were charged 79 ml of xylene, 138.16 g (1 mol) of 4-methoxybenzyl alcohol, 3.30 g (0.01 mol) of sodium tungstate.dihydrate (Na2WO4.2H2O) and 3.40 g (0.01 mol) of tetrabutyl ammonium hydrogen sulfate. Then, to the mixture were added 4.68 g (0.03 mol) of sodium dihydrogen phosphate and 7.16 g (0.02 mol) of disodium hydrogen phosphate, and a pH value of the reaction mixture was adjusted to pH 6.0. Next, an inner temperature of the reaction mixture was maintained from 94 to 95° C., and 94.33 g (1.56 mol) of 60% aqueous hydrogen peroxide was added dropwise to the mixture with 18 g (0.3 mol)/hr, while maintaining the pH of the reaction mixture to 5.5 to 6.5 by using 8 mol/L aqueous sodium hydroxide solution. After completion of the reaction, the resulting reaction mixture was cooled to room temperature, and the organic layer was separated as a solution. The resulting organic layer solution was washed with 1 mol/L sodium hydroxide solution, and the solvent, xylene was distilled off under reduced pressure. The resulting concentrate (crude anisaldehyde) was purified by distillation (109° C./1.3 kPa) to obtain 118.28 g of anisaldehyde as colorless liquid (obtained yield: 86.9%, based on anisalcohol).

Workup

  1. customIn a glass-made reaction vessel equipped with a thermometer
  2. temperaturewhile maintaining the pH of the reaction mixture to 5.5 to 6.5
  3. customAfter completion of the reaction
  4. customthe resulting reaction mixture
  5. temperaturewas cooled to room temperature
  6. customthe organic layer was separated as a solution
  7. washThe resulting organic layer solution was washed with 1 mol/L sodium hydroxide solution
  8. distillationthe solvent, xylene was distilled off under reduced pressure
  9. concentrationThe resulting concentrate (crude anisaldehyde)
  10. distillationwas purified by distillation (109° C./1.3 kPa)
  11. customto obtain

Sources & evidence

ORD record
ord-58898628ff9341d0a8449b5c49240fcd
Source dataset
uspto-grants-2013_12
Patent number
US08618335B2

Reaction notes

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