O.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=[O:9].[CH2:14](O)[CH2:15][OH:16].ClCCl>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:8]2[O:16][CH2:15][CH2:14][O:9]2)[CH:10]=1In a flask equipped with a Dean-Stark water separator, 5-chloro-2-nitrobenzaldehyde (12.0 g, 64.7 mmol), ethylene glycol (8.0 g, 129.3 mmol) and p-toluenesulfonic acid (0.2 g) were dissolved in toluene (150 mL). The mixture was stirred at reflux for 8 hours. Dichloromethane was added and the organic phase was washed with saturated sodium bicarbonate and brine, then dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 2-(5-chloro-2-nitrophenyl)-1,3-dioxolane (13.4 g, yield 90.0%).
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