Hydrochloric Acid → 2-(Chloromethyl)-4-nitrophenol

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A 5-necked flask equipped with mechanical overhead stirrer, gas inlet tube, reflux condenser and a thermometer was charged with 4-nitrophenol (100 g, 0.72 mol). Concentrated HCl 932%, 1.3 L), conc. H2SO4 (98%, 10 mL) and formaldehyde dimethylacetal (152.4 g, 2 moles) were added and the mixture was heated to 70° C. Gaseous HCl was bubbled through the mixture for 4 hours. During this time a thick white precipitate formed. The suspension was cooled to 0° C., the precipitate was isolated by vacuum filtration and the yellow powder was dried over night under vacuum to give 108.76 g of slightly impure 2-chloromethyl-4-nitrophenol (about 76% yield).

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