1: 90 percent / 4 M NaOH / ethanol / 2 h / Heating 2: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h 3: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 4: 31 percent / KI / toluene / 100 - 110 °C 5: 60 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / 0.33 h / 160 °C View Scheme

1: 90 percent / 4 M NaOH / ethanol / 2 h / Heating 2: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h 3: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 4: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 5: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

aluminium trichloride in carbon disulfide T=40 - 50°C; 0.5 h;

sodium hydroxide in ethanol 2 h; Heating;

hydrogenchloride