Iodine → 1-(4-hydroxy-3-iodophenyl)ethanone

Participants

Reaction Steps

4.08 g (corresponding to 30.0 mmol) of 4′-hydroxyacetophenone was dissolved in 250 mL of 28% aqueous ammonium solution, and a solution of 7.61 g (corresponding to 30.0 mmol) of iodine and 24.3 g (corresponding to 146 mmol) of potassium iodide in 60 mL of water was added thereto. The resulting solution was stirred at room temperature for 22.5 hours. After the completion of the reaction, the reaction mixture was concentrated, diluted with water, and then extracted three times with ethyl acetate. The combined ethyl acetate layers were washed once with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. To the resulting concentrates, 60 mL of water and 40 mL of 8 mol/L sodium hydroxide solution were added, sufficiently mixed, and filtered to remove insoluble matters. Then, conc. hydrochloric acid was added to the filtrate to make it acidic, and the precipitates were filtered and dried under reduced pressure. The resulted precipitates were dissolved in a mixed solution of chloroform and ethyl acetate, and then water was added thereto, and extracted with chloroform for five times. The combined chloroform layers were dried over anhydrous sodium sulfate, and then the solvent was distilled under reduced pressure, to obtain 4.00 g (corresponding to 15.3 mmol) of 4′-hydroxy-3′-iodoacetophenone (FIG. 3, Step 4).

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