in toluene T=60°C; 1 h;

in ethyl acetate T=0 - 80°C; 2.5 h;

aluminium trichloride in ethanol; dichloromethane; water; Petroleum ether

carbon disulfide; AlCl3, aluminium chloride T=50°C; Friedel-Crafts reaction;

Pd-BaSO4; perchloric acid; acetic acid T=95°C; Hydrogenation;

1: palladium/BaSO4; acetic acid; aqueous HClO4 / 95 °C / Hydrogenation 2: aqueous HCl View Scheme

hydrogenchloride

1.1: bromine / chloroform 1.2: 24 h / 20 °C / pH 8 2.1: sodium ethanolate / ethanol / Cooling with ice 2.2: 8.17 h / 35 - 75 °C 3.1: sodium hydroxide / water / 4 h 3.2: 3 h / 100 °C / pH 1 View Scheme

1.1: bromine / chloroform 1.2: 24 h / 20 °C / pH 8 2.1: sodium ethanolate / ethanol / Cooling with ice 2.2: 8.17 h / 35 - 75 °C 3.1: sodium hydroxide / water / 4 h 3.2: 3 h / 100 °C / pH 1 4.1: L-(+)-tartaric acid / isopropyl alcohol / 0.5 h / Heating; Resolution of racemate 4.2: pH 7 - 8 / Resolution of racemate 4.3: 0.5 h / Reflux; Resolution of racemate View Scheme

1.1: bromine / chloroform 1.2: 24 h / 20 °C / pH 8 2.1: sodium ethanolate / ethanol / Cooling with ice 2.2: 8.17 h / 35 - 75 °C View Scheme