Hydrogen Peroxide → 3-(4-Chlorophenoxy)-2-methylpropane-1,2-diol

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)).

1. temperatureThe mixture was heated to 40° C.
2. stirringstirred for 9 hours
3. stirringby stirring at 70° C. for 1 hour
4. temperaturethe mixture was heated
5. washwashed with water at a temperature about 60° C
6. temperatureThe reaction mixture was cooled with ice
7. filtrationthe precipitated crystals were collected by filtration
8. customThe resulting crystals were dried under reduced pressure

ORD record

ord-08ad78e6bee549bf906bcf9da5fabf3e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598358B2