2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 0.166667 h; Heating;

toluene-4-sulfonic acid in benzene 0.5 h; Heating;

1: 99 percent / HCl / 1 h / Ambient temperature 2: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 3: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 4: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 5: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 6: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 7: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme

1: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 2: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 3: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 4: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 5: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 6: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme

1: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 2: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme

1: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 2: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 3: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 4: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme

1: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 2: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 3: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 4: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 5: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme