1: 90 percent / lithium aluminum hydride / diethyl ether / 24 h / Ambient temperature 2: 90 percent / phosphorus tribromide / benzene 3: 90 percent / methanol / Heating 4: 85 percent / potassium hydroxide / H2O; ethane-1,2-diol / Heating View Scheme

1: 90 percent / lithium aluminum hydride / diethyl ether / 24 h / Ambient temperature 2: 90 percent / phosphorus tribromide / benzene 3: 90 percent / methanol / Heating 4: 85 percent / potassium hydroxide / H2O; ethane-1,2-diol / Heating 5: PCl5 / benzene / 0.5 h / Ambient temperature 6: 82 percent / SnCl4 / benzene / 1.) 0 deg C, 30 min; 2.) rt, 90 min View Scheme