Carbon Tetrachloride → 2-Chloro-4-(2,2,2-trichloro-1-hydroxyethyl)phenol

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Reaction Steps

3-Chloro-4-hydroxy benzaldehyde (15.6 g, 0.1 mol) was added to 200 ml of dimethylformamide, a mixture was stirred, aluminium (8.09 g, 0.3 mol) and leadbromide (3.67 g, 0.01 mmol) were added thereto. CCl4 (61.53 g, 0.4 mol) was slowly added to the reaction mixture. The mixture was stirred at room temperature for 10 hours, and unreacted solid was filtered to remove therefrom. After sequentially adding 5% HCl, ethylacetate and water thereto, the mixture was extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and distilled. The resulting residue was subjected to column chromatography (ethyl acetate: n-hexane=1:4) to obtain the title compound (24.55 g, 89%).

Provenance & Evidence