1.1: toluene-4-sulfonic acid / toluene / 1 h / 110 °C 2.1: lithium diisopropyl amide / 0.5 h / 0 - 5 °C 2.2: 4 h / 0 - 30 °C 3.1: hydrogenchloride / diethyl ether / 30 °C 4.1: 12 h / 100 °C 5.1: 10 palladium on activated charcoal; hydrogen / 10 h / 30 °C 6.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere 7.1: sodium hydroxide / water / pH 7.5 - 8 7.2: 0.5 h / 0 °C 7.3: 3 h / 25 °C 8.1: 5 Pd(II)/C(eggshell); hydrogen / ethanol; water / 3 h / 25 - 30 °C / 1838.93 - 2206.72 Torr / Autoclave 9.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme

1.1: lithium diisopropyl amide / 0.5 h / 0 - 5 °C 1.2: 4 h / 0 - 30 °C 2.1: hydrogenchloride / diethyl ether / 30 °C 3.1: 12 h / 100 °C 4.1: 10 palladium on activated charcoal; hydrogen / 10 h / 30 °C 5.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme

1.1: toluene-4-sulfonic acid / toluene / 1 h / 110 °C 2.1: lithium diisopropyl amide / 0.5 h / 0 - 5 °C 2.2: 4 h / 0 - 30 °C 3.1: hydrogenchloride / diethyl ether / 30 °C 4.1: 12 h / 100 °C 5.1: 10 palladium on activated charcoal; hydrogen / 10 h / 30 °C 6.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme

hydrogenchloride; sodium hydroxide 1.) methylene chloride, water; 2.) diisopropyl ether; Yield given. Multistep reaction;

hydrogenchloride; sodium hydroxide in dichloromethane; ethyl acetate

sodium hydrogencarbonate in water; toluene T=20°C; 0.333333 - 0.666667 h; Product distribution / selectivity;

benzotriazol-1-ol; triethylamine in dichloromethane T=25 - 30°C; 16 h;

1: 95 percent / K2CO3, 25percent ethylmethylphosphinic anhydride / H2O; CH2Cl2 2: H2 / 10percent Pd/C / methanol / 0.5 h / 750.06 - 3750.3 Torr / Ambient temperature View Scheme

hydrogenchloride; sodium hydroxide in dichloromethane; ethyl acetate

hydrogen; palladium on activated charcoal in ethanol T=30°C; 1 h; Yield given;