Acetone → 3-(4-Bromophenoxy)-2-methylpropane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

2-[(4-Bromophenoxy)methyl]-2-methyloxirane (72.9 g, 300 mmol), acetone (360 ml), water (180 ml), and sulfuric acid (7.3 ml) were mixed and stirred at 60° C. for 1 hour. After cooling, the mixture was concentrated under reduced pressure. Ethyl acetate (360 ml) and a saturated sodium bicarbonate solution were added to the concentrated residue, followed by extraction. Thereafter, the ethyl acetate layer was dried over anhydrous sodium sulfate. Ethyl acetate (102 ml) was added to the resulting crude product and heated to dissolve the crude product. The resulting solution was cooled to room temperature, and then hexane (204 ml) was added thereto, followed by stirring at a temperature 10° C. or less for 1 hour. The precipitated crystals were collected by filtration and then washed with a mixture of ethyl acetate (24 ml) and hexane (48 ml). The resulting crystals were dried under reduced pressure, obtaining 44.0 g of the objective product (yield: 56%).

Provenance & Evidence