Ethylene Glycol → 2-(3-Bromophenyl)-2-methyl-1,3-dioxolane

Participants

Reaction Steps

A mixture of 3-bromoacetophenone (10 mL, 75.6 mmol), ethylene glycol (10.1 mL, 181 mmol), and p-toluenesulfonic acid hydrate in toluene (120 mL) was heated with azeotropic removal of water. After 4 hours, a second portion of ethylene glycol was added and the mixture heated at refluxed for 48 hours. The reaction was cooled to room temperature and washed with saturated aqueous sodium bicarbonate solution and brine, and dried over sodium sulfate. Removal of the volatiles in vacuo provided a residue that was purified by flash chromatography. Concentration of the product-rich fractions afforded 2-(3-bromophenyl)-2-methyl-[1,3]dioxolane as a clear oil. Yield: 2.44 g.

Provenance & Evidence