1,2-dichloro-5,6-dicyanobenzo-1,4-quinone in toluene T=100°C; 0.5 h;

1: 87 percent / H2 / Pd/C / ethyl acetate / 48 h 2: 82 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 0.17 h / Heating 3: 9 percent / 1,2-dichloro-5,6-dicyanobenzo-1,4-quinone / toluene / 0.5 h / 100 °C View Scheme

1: 75 percent / ethyl acetate / 4 h / Heating 2: 87 percent / H2 / Pd/C / ethyl acetate / 48 h 3: 82 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 0.17 h / Heating 4: 9 percent / 1,2-dichloro-5,6-dicyanobenzo-1,4-quinone / toluene / 0.5 h / 100 °C View Scheme

1: 82 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / 0.17 h / Heating 2: 9 percent / 1,2-dichloro-5,6-dicyanobenzo-1,4-quinone / toluene / 0.5 h / 100 °C View Scheme

diphenyl-phenyl carbinol; trifluoroacetic acid; trifluoroacetic anhydride 12 h; Heating;