2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=25°C; 5.5 h;

lithium aluminium tetrahydride; diethyl ether

lithium aluminium tetrahydride in tetrahydrofuran 1.) from -20 deg C to 10 deg C, 1 h, 2.) 10 deg C, 1 h; Yield given;

1: 1.) LDA / 1.) THF, -70 deg C, 10 min, 2.) THF, -70 deg C, 30 min 2: trifluoroacetic acid / CH2Cl2 / Ambient temperature 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 8 h / Heating 4: lithium aluminum hydride / tetrahydrofuran / 1.) from -20 deg C to 10 deg C, 1 h, 2.) 10 deg C, 1 h View Scheme

1: 1.) LDA / 1.) THF, -70 deg C, 10 min, 2.) THF, -70 deg C, 30 min 2: trifluoroacetic acid / CH2Cl2 / Ambient temperature 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 8 h / Heating 4: lithium aluminum hydride / tetrahydrofuran / 1.) from -20 deg C to 10 deg C, 1 h, 2.) 10 deg C, 1 h View Scheme

1: trifluoroacetic acid / CH2Cl2 / Ambient temperature 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 8 h / Heating 3: lithium aluminum hydride / tetrahydrofuran / 1.) from -20 deg C to 10 deg C, 1 h, 2.) 10 deg C, 1 h View Scheme

1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 8 h / Heating 2: lithium aluminum hydride / tetrahydrofuran / 1.) from -20 deg C to 10 deg C, 1 h, 2.) 10 deg C, 1 h View Scheme

lithium aluminium tetrahydride

lithium aluminium tetrahydride; diethyl ether