1,2-Ethanedithiol → 2-Benzoyloxymethyl-1,3-dithiolane

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Reaction Steps

A mixture of 2-benzoyloxyacetaldehyde (example (5.65 g), 1,2-ethanedithiol (3 ml) and paratoluenesulfonic acid (200 mg) in toluene (250 ml) was heated at refluxing under water removal conditions using a Dean Stark apparatus for 4 hours. The mixture was cooled to room temperature, washed first with saturated aqueous NaHCO3 solution (1×60 ml), then with water (2×60 ml), and dried over reduced pressure. The residue was purified by chromatography on silica gel using hexane:ethyl acetate (9:1) as eluant to give 5.2 g of pure product which was characterized by 1H- and 13C-NMR spectroscopy.

Provenance & Evidence