Citric Acid → HCID 21713169, compound

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Reaction Steps

Sodium 4-(pyridine-4-carbonyl)benzenesulfinate (3.33 g, 14.04 mmol) was dissolved in water (60 ml). This solution was shaken with iodine (3.56 g, 34.29 mmol) in dishloromethane (40 ml). The dichloromethane layer turned from deep pink to orange. The dishloromethane layer was dried over magnesium sulfate and filtered into a flask containing 2-propylacrylic acid (0.8 g, 7.02 mmol). The solution was stirred overnight at room temperature and then cooled to 0° C. Triethylamine (4.0 ml, 28.08 mmol) was added and the solution was allowed to warm to room temperature over 2 hours. The mixture was acidified to pH 4 by addition of 10% citric acid. The layers were separated and the product was extracted with 2M sodium hydroxide (3×50 ml). The combined aqueous phase was washed with ethyl acetate (50 ml), the acidified to pH 4 with citric acid. The product was extracted into ethyl acetate (2×50 ml), then back into 1M hydrochloric acid (100 ml). The aqueous layer was washed with ethyl acetate (2×50 ml), then solid sodium hydrogen carbonate was added to pH 4. The product was extracted into dichloromethane (2×50 ml) and the combined organic layers were washed with brine (20 ml), dried over magnesium sulfate, filtered and evaporated to give the title compound (0.60 g, 24%).

Provenance & Evidence