Ethylene Glycol → 2-(8-Bromooctyl)-1,3-dioxolane

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Reaction Steps

9-Bromononanal (28.0 g, assumed 120 mmol), ethylene glycol (33.6 mL, 600 mmol) and para-toluenesulphonic acid (2.7 g, 13 mmol) in toluene (210 mL) were heated at reflux for 20 hours. The reaction was cooled to RT and quenched with saturated aqueous sodium bicarbonate solution (300 mL). The resultant mixture was extracted with diethyl ether (×2). The combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, water and brine (100 mL). The organic phase was dried (magnesium sulphate), filtered and evaporated under reduced pressure to afford the title compound (25.2 g, 79%).

Provenance & Evidence