Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → N-(3-formylphenyl)acetamide

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A mixture of N-(3-[1,3]Dioxolan-2-yl-phenyl)-acetamide (7.8 g, 0.037 mol) and pyridinium-p-toluenesulfonate (2.8 g, 0.011 mol) in acetone-water (4:1, 400 mL) was refluxed for 1 hr. The solution was then cooled to room temperature, and the bulk of the solvent (˜90%) removed under reduced pressure. The remaining solution was then extracted with EtOAc, and the combined extracts washed with saturated NaHCO3, brine, and dried with MgSO4. Evaporation of the solvent gave N-(3-Formyl-phenyl)-acetamide (5.98 g, 98%) as an orange oil. 1H NMR (CDCl3) δ 2.22 (s, 3H), 7.46 (t, J=8 Hz, 1H), 7.59 (d, J=8 Hz, 1H), 7.89 (d, J=8 Hz, 1H), 8.07 (s, 1H), 8.69 (br s, 1H), 9.94 (s, 1H). 13C NMR (CDCl3) δ 193.9, 171.0, 140.8, 138.5, 131.2, 127.5, 127.1, 122.0, 26.0.

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