1: With potassium carbonate; copper(l) iodide in toluene T=148°C; Ullmann type reaction; 21 h; Heating / reflux; 2: With hydrogenchloride in water pH=1 - 2; 3: With sodium hydroxide in water pH=11 - 12;

hydrogenchloride in diethyl ether

1: in ethyl acetate T=20°C; Heating / reflux; 2: With hydrogenchloride in acetic acid n-butyl ester T=15 - 20°C; 2 h; Product distribution / selectivity;

1: With sodium hydroxide; water in ethyl acetate 2: With hydrogenchloride in ethyl acetate 1 h;

hydrogenchloride in ethanol

1: 3-hydroxy-3-phenylpropyl 4-toluenesulfonate With 3 A molecular sieve; oxygen; (-)-sparteine; palladium diacetate in toluene T=80°C; P=760 Torr; 36 h; 2: methylamine With water in tetrahydrofuran T=65°C; 3: ortho-cresol With hydrogenchloride; triphenylphosphine; diethylazodicarboxylate in diethyl ether T=-10 - 0°C;

in ethanol; water T=130°C; 3 h;

hydrogenchloride in isopropyl alcohol T=0 - 5°C; 1 - 1.5 h; Heating / reflux; Product distribution / selectivity;

1.1: DCC; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 2.1: Candida rugosa lipase; MgCl2 / H2O; diisopropyl ether / 24 h / 30 °C 3.1: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / 20 °C 4.1: 85 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C / cooling 5.1: DEAD; PPh3 / diethyl ether; toluene / 30 h / -10 °C 5.2: 78 percent / diethyl ether; toluene / 2.5 h / -10 °C 6.1: 82 percent / H2O; tetrahydrofuran / 4 h / 60 - 65 °C 7.1: 99 percent / HCl / diethyl ether View Scheme

1: in tetrahydrofuran; water T=65°C; 3 h; 2: With hydrogenchloride in diethyl ether optical yield given as percent ee;