Benzaldehyde dimethyl acetal → 2-Phenyl-1,3-oxathiolane

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Reaction Steps

To an oven-dried 250 mL flask fitted with a magnetic stirring bar and reflux condenser was introduced 0.4 g of Montmorillonite KSF, 1.65 g (10.8 mmol) of benzaldehyde dimethyl acetal in 35 mL of THF, followed by 1.0 g (10.8 mmol) of 3-mecapto-1-propanol in 5 mL of THF. The mixture was refluxed under nitrogen for 12 hours. After cooling to room temperature and filtered, the filtrate was washed with saturated NaHCO3 (2×20 mL), saturated NaCl (20 mL) and dried over MgSO4 (anhydrous). The solvent was evaporated; a chromatograph using silica gel [elution with Hexane/Et2O (70/30)] was obtained on the residue, yielding 1.9 g (97%) of 2-phenyl-1,3-oxathiolane. 1H-NMR (CDCl3): δ 1.74 (m, 1H), 2.11 (m, 1H), 2.82, (m, 1H), 3.22 (m, 1H), 3.81 (m, 1H), 4.35 (m, 1H), 5.80 (s, 1H), 7.36 (m, 3H), 7.49 (m, 2H). 13C-NMR (CDCl3): δ 25.73, 29.26, 70.74, 126.19, 128.46, 128.53, 139.52.

Provenance & Evidence