2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 2.5 h; Heating;

1: 82 percent / AlCl3 / CS2 / 6 h / 0 °C 2: 100 percent / NaBH4 / ethanol; H2O / 20 h / Ambient temperature 3: 71 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 4: 70 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating 5: 58 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 2.5 h / Heating View Scheme

1: 95 percent / HI / acetic acid / 6 h / Heating 2: 82 percent / AlCl3 / CS2 / 6 h / 0 °C 3: 100 percent / NaBH4 / ethanol; H2O / 20 h / Ambient temperature 4: 71 percent / p-toluenesulfonic acid / benzene / 2 h / Heating 5: 70 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating 6: 58 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 2.5 h / Heating View Scheme

1: 76 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating 2: 58 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 2.5 h / Heating View Scheme

1: 70 percent / hydrazine monohydrate, KOH / bis-(2-hydroxy-ethyl) ether / 6 h / Heating 2: 58 percent / 2,3-dichloro-5,6-dicyanoquinone / benzene / 2.5 h / Heating View Scheme