1: hydrogen / Raney-Ni / tetrahydrofuran / 30 °C / 8250.83 Torr 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone; acetic acid / toluene / 5 h / 40 °C View Scheme

1: 90.7 percent / DDQ / CH2Cl2 / 20 °C 2: 88.2 percent / TsOH*H2O / benzene / 1 h / Heating 3: LiAlH4 / tetrahydrofuran / 45 - 50 °C View Scheme

1: 90.7 percent / DDQ / CH2Cl2 / 20 °C 2: 88.2 percent / TsOH*H2O / benzene / 1 h / Heating View Scheme