Specific Examples NH OH (1)NaNO, H2SOL R=Br 3-Bromophenol 66% (2)H3O, heat R=NO,3-Nitrophenol 80% R NH2 Br (1) NaNO2, H2So 0-5℃ (2)H3O, heat 2-Bromo-4-methylphenol 80-92% CH3 CH 214B INDUSTRIAL SYNTHESIS Hydrolysis of chlorobenzene Cl ONa Naoh 350℃( high pressure
Specific Examples: 21.4B INDUSTRIAL SYNTHESIS 1. Hydrolysis of Chlorobenzene Cl 350℃ (high pressure) ONa NaOH HCl OH NH2 R NH2 OH R OH Br CH3 Br CH3 (1) NaNO2 , H2SO4 0-5℃ (2) H3O + , heat (1) NaNO2 , H2 SO4 0-5℃ (2) H3O + , heat R = Br 3-Bromophenol 66% R = NO2 3-Nitrophenol 80% 2-Bromo-4-methylphenol 80-92%
2. Alkali Fusion of sodium benzenesul fonate SOrNa ONa Naoh HCI 350℃( high pressure) Sodiu benzenesulfonate (苯磺酸钠) 3. From Cumene hydroperoxide Friedel-Crafts alkylation HaPO Ch2-CHCa3 250C pressure Cumene (异丙基苯) Oxidization: 5-135℃ 0-0-H Cumene hydroperoxide (过氧化异丙基苯
2. Alkali Fusion of Sodium Benzenesulfonate SO3 Na 350℃ (high pressure) ONa NaOH HCl OH benzenesulfonate (苯磺酸钠） Sodium 3. From Cumene Hydroperoxide + CH2 =CHCH3 250℃ H3 PO4 pressure Cumene (异丙基苯) Friedel-Crafts alkylation: Oxidization: + O2 95-135℃ O O H Cumene hydroperoxide (过氧化异丙基苯)
Hydrolytic rearrangement 0-0-H H, HO Acetone oH 50-90℃ (丙酮) Corresponding mechanism Friedel-Crafts alkylation: Oxidization O O-0·+ O-0-H
Corresponding Mechanism: Friedel-Crafts alkylation: H + H - H + Oxidization: H R O2 O O O O + O O H + C• Hydrolytic rearrangement: O O H H + , H2O 50-90℃ OH O + Acetone (丙酮）