Hydrogen Peroxide → 1,2-Propanediol, 3-(p-chlorophenoxy)-2-methyl-

Participants

Reaction Steps

A mixture of β-methallyl alcohol (50 g, 693 mmol) and sodium tungstate dihydrate (460 mg, 1.4 mmol) was stirred at room temperature. A 30% hydrogen peroxide solution (86.5 g, 763 mmol) was added thereto dropwise over a period of 5 minutes. The mixture was heated to 40° C. and stirred for 9 hours. Potassium carbonate (79.7 g, 576 mmol) and 4-chlorophenol (52.4 g, 407 mmol) were added to the resulting reaction mixture, followed by stirring at 70° C. for 1 hour. After adding toluene (390 ml), the mixture was heated and then washed with water at a temperature about 60° C. The reaction mixture was cooled with ice, and then the precipitated crystals were collected by filtration. The resulting crystals were dried under reduced pressure, obtaining 60.0 g of 3-(4-chlorophenoxy)-2-methylpropane-1,2-diol (yield: 68% (based on 4-chlorophenol)).

Provenance & Evidence