1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 5: SOCl2 / 1 h / Heating 6: 63 percent / pyridine / dimethyl ether / overnight View Scheme

1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 5: SOCl2 / 1 h / Heating 6: 25percent aq. NH4OH 7: 56 percent / SOCl2, dimethylformamide / 1.5 h / Ambient temperature View Scheme

1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C View Scheme

AlCl3, aluminium chloride in hexane T=-60 - -40°C; 3.5 h;

aluminium trichloride in dichloromethane other solvents: dichloroethane, nitromethane; Yield given. Yields of byproduct given;

1: AlCl3 / 45 °C 2: NaBH4 / propan-1-ol / 4 h / 30 - 35 °C 3: p-toluenesulfonic acid / toluene / Heating View Scheme

1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h View Scheme

1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol 3: AlCl3 / 1,2-dichloro-ethane / 0.5 h 4: aq. NaOH, Br2 / dioxane / 3 h / 35 - 40 °C 5: SOCl2 / 1 h / Heating View Scheme

1: AlCl3 / 45 °C 2: hydrazine hydrate / bis-(2-hydroxy-ethyl) ether / or in 1:1 mixture of triethanolamine and glycerol View Scheme