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

반응식

[N+:1]([C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[ClH:11].COC[O:15][CH3:16]>OS(O)(=O)=O>[Cl:11][CH2:7][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:16]=1[OH:15]

참가 물질

반응 조건

온도: 70 °C

실험 절차

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).