Hydrogen Peroxide → 4-Methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence