hydrogenchloride T=100°C; 2 h;

1.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 1.2: 76 percent / hexane; diethyl ether / 1 h / -78 - 20 °C 2.1: 79 percent / p-TsOH / H2O; toluene / 4 h / 140 °C 3.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 3.2: 54 percent / hexane; diethyl ether / 1 h / -78 - 20 °C 4.1: 82 percent / hydrochloric acid / 2 h / 100 °C View Scheme

1.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 1.2: 54 percent / hexane; diethyl ether / 1 h / -78 - 20 °C 2.1: 82 percent / hydrochloric acid / 2 h / 100 °C View Scheme

1.1: 79 percent / p-TsOH / H2O; toluene / 4 h / 140 °C 2.1: n-butyllithium / hexane; diethyl ether / 0.5 h / -78 °C 2.2: 54 percent / hexane; diethyl ether / 1 h / -78 - 20 °C 3.1: 82 percent / hydrochloric acid / 2 h / 100 °C View Scheme

1: 80 percent / p-toluene sulfonic acid / toluene / 4 h / Heating 2: 1.) Na, CH3OH / benzene / 1.) 1 h, reflux, 2.) 16 h, r.t. 3: 3.5 percent HCl / 1 h / Heating View Scheme

dihydrogen peroxide in water