1: With sodium hydroxide in dichloromethane; water T=25 - 30°C; 2: With hydrogenchloride in water; isopropyl alcohol

1: in n-heptane T=40 - 50°C; Heating / reflux; 2: With sodium hydroxide in n-heptane T=0 - 10°C; pH=10 - 10.5; 0.25 h; 3: With hydrogenchloride in n-heptane T=5 - 10°C; pH=1; 1 h;

hydrogenchloride in dichloromethane; water T=0 - 3°C; 2 - 3 h; Product distribution / selectivity;

thionyl chloride T=0 - 25°C; 13 h; Inert atmosphere;

thionyl chloride T=0 - 25°C; 13 h; Inert atmosphere;

hydrogenchloride; sodium hydroxide in dichloromethane; ethyl acetate

1.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere 2.1: sodium hydroxide / water / pH 7.5 - 8 2.2: 0.5 h / 0 °C 2.3: 3 h / 25 °C 3.1: 5 Pd(II)/C(eggshell); hydrogen / ethanol; water / 3 h / 25 - 30 °C / 1838.93 - 2206.72 Torr / Autoclave 4.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme

1.1: sodium hydroxide / water / pH 7.5 - 8 1.2: 0.5 h / 0 °C 1.3: 3 h / 25 °C 2.1: 5 Pd(II)/C(eggshell); hydrogen / ethanol; water / 3 h / 25 - 30 °C / 1838.93 - 2206.72 Torr / Autoclave 3.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme

1: 5 Pd(II)/C(eggshell); hydrogen / ethanol; water / 3 h / 25 - 30 °C / 1838.93 - 2206.72 Torr / Autoclave 2: 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 6.1: sodium hydroxide / water / pH 7.5 - 8 6.2: 0.5 h / 0 °C 6.3: 3 h / 25 °C 7.1: 5 Pd(II)/C(eggshell); hydrogen / ethanol; water / 3 h / 25 - 30 °C / 1838.93 - 2206.72 Torr / Autoclave 8.1: thionyl chloride / 13 h / 0 - 25 °C / Inert atmosphere View Scheme