Ethylene Glycol → 4-((1,3-Dioxolan-2-yl)methyl)benzonitrile

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Reaction Steps

To a stirred solution of 4-(2-hydroxyethyl)benzonitrile (1.09 g, 7.41 mmol) in DCM (20 mL), was added Dess-Martin Periodinane (3.77 g, 8.84 mmol), and the reaction mixture stirred at room temperature for 1 hour. A 1:1 mixture of saturated aqueous sodium hydrogen carbonate and saturated sodium thiosulfate was added, and the bi-phasic mixture stirred for 1 hour. The organic phase was separated, and the aqueous phase extracted with further DCM (×3). The combined organic extracts were dried with anhydrous magnesium sulphate, and the solvent evaporated at reduced pressure. The crude material was dissolved in toluene (40 mL) and ethylene glycol (2.29 g, 37.05 mmol), and p-toluenesulfonic acid (0.14 g, 0.74 mmol) added. The mixture was heated under Dean and Stark conditions for 2 hours. The solvent was evaporated under reduced pressure, and the residue partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic phase was removed, and the aqueous phase was extracted with further ethyl acetate (×3). The combined organic phases were dried with anhydrous magnesium sulphate, and the solvent evaporated at reduced pressure to afford the title compound (1.40 g, 99%).

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