ammonium hydroxide in water; acetonitrile

iron(III) chloride in tetrahydrofuran; water; toluene

iron(III) chloride in tetrahydrofuran 0.5 h; Ambient temperature; Yield given;

1: AlCl3 / 2 h / 90 °C 2: NaBH4 / methanol / 0.5 h / 0 °C 3: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C 4: boron trifluoride etherate / toluene / 2 h / 60 °C 5: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 98 percent / SOCl2 / CH2Cl2 / 2 h / 50 °C 2: AlCl3 / 2 h / 90 °C 3: NaBH4 / methanol / 0.5 h / 0 °C 4: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C 5: boron trifluoride etherate / toluene / 2 h / 60 °C 6: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: NaBH4 / methanol / 0.5 h / 0 °C 2: 95 percent / 2.5 N NaOH / tetrahydrofuran / 3 h / 70 °C 3: boron trifluoride etherate / toluene / 2 h / 60 °C 4: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: boron trifluoride etherate / toluene / 2 h / 60 °C 2: aq. FeCl3 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme