Acetone → 4-[(4-Bromophenoxy)methyl]-2,2,4-trimethyl-1,3-dioxolane

Participants

Reaction Steps

3-(4-Bromophenoxy)-2-methylpropane-1,2-diol (261 mg, 1.00 mmol), acetone (77 mg, 1.3 mmol), tetrahydrofuran (5 mL), and a boron trifluoride diethyl ether complex (3 drops) were mixed. The mixture was stirred at room temperature for 67 hours, and acetone (102 mg, 1.76 mmol) was added thereto, followed by stirring for 2 hours. Sodium carbonate, ethyl acetate, and water were added to the reaction mixture to conduct extraction. The organic layer was washed with a saline solution twice. A residue was obtained by concentrating the organic layer under reduced pressure, and the residue was subjected to chromatography refining (methylene chloride) using silica gel, obtaining 121 mg of the objective compound (yield: 40%).

Provenance & Evidence