potassium permanganate in water; acetone 1.5 h; Heating;

1: 87 percent / benzene; diethyl ether / 1.) 2 h, room temperature, 2.) 3 h, reflux 2: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 3: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 4: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme

1: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 2: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 3: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme

1: 87 percent / benzene; diethyl ether / 1.) 2 h, room temperature, 2.) 3 h, reflux 2: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 3: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 4: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme

1: 70 percent / NaH / dimethylformamide / 6 h / 100 °C 2: 87 percent / benzene; diethyl ether / 1.) 2 h, room temperature, 2.) 3 h, reflux 3: N-bromosuccinimide (NBS), benzoyl peroxide (BPO) / CCl4 / 8 h / Heating 4: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 5: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme

1: 1.) AcOK; 2.) 2 N HCl / 1.) AcOH, 8 h, reflux; 2.) reflux, 30 min 2: 97 percent / KMnO4 / acetone; H2O / 1.5 h / Heating View Scheme

potassium hydroxide in water 2 h; Heating;