1: aq.HCl / benzene / 24 h / Heating 2: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h View Scheme

hydrogenchloride in benzene 24 h; Heating;

1: aq.HCl / benzene / 24 h / Heating 2: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 3: 91 percent / LAH / tetrahydrofuran / 2 h / Heating View Scheme

hydrogen; palladium on activated charcoal in methanol 6 h; Ambient temperature;

1: aq.HCl / benzene / 24 h / Heating 2: 1.) NaH / 1.)a) THF, RT, 10 min, b) reflux, 15 min, 2.) THF, reflux, 1.5 h 3: 91 percent / LAH / tetrahydrofuran / 2 h / Heating 4: 46 percent / p-toluenesulfonic acid / benzene / Heating View Scheme

1: 70 percent / CHCl3 / 10 h / Ambient temperature 2: potassium hydroxide / H2O / 6 h / Heating 3: H2O; CHCl3 / 2 h / 20 °C 4: LiAlH4 / tetrahydrofuran / 12 h / Heating 5: 6N HCl / H2O / 12 h / Ambient temperature 6: 9 percent / hydroxylamine hydrochloride, sodium acetate / methanol / 8 h / Ambient temperature View Scheme

1: 70 percent / CHCl3 / 10 h / Ambient temperature 2: potassium hydroxide / H2O / 6 h / Heating 3: H2O; CHCl3 / 2 h / 20 °C 4: LiAlH4 / tetrahydrofuran / 12 h / Heating 5: 6N HCl / H2O / 12 h / Ambient temperature 6: 9 percent / hydroxylamine hydrochloride, sodium acetate / methanol / 8 h / Ambient temperature 7: LiAlH4 / tetrahydrofuran; diethyl ether / 3 h / Heating View Scheme

1: 70 percent / CHCl3 / 10 h / Ambient temperature 2: potassium hydroxide / H2O / 6 h / Heating 3: H2O; CHCl3 / 2 h / 20 °C 4: LiAlH4 / tetrahydrofuran / 12 h / Heating 5: 6N HCl / H2O / 12 h / Ambient temperature View Scheme

in benzene Heating;

1: benzene / Heating 2: KOH / ethanol / Heating 3: K2CO3 View Scheme