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

1: AlCl3 / nitrobenzene / 6 h / Ambient temperature 2: Zn(Hg), HCl / acetic acid; toluene / 3 h / Heating 3: 1.) (COCl)2, 2.) AlCl3 / 1.) CH2Cl2, RT, 1 h, 2.) CS2, reflux, 30 min 4: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 5: PTSA / benzene / 0.5 h / Heating 6: DDQ / benzene / 0.17 h / Heating View Scheme

1: PTSA / benzene / 0.5 h / Heating 2: DDQ / benzene / 0.17 h / Heating View Scheme

1: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: PTSA / benzene / 0.5 h / Heating 3: DDQ / benzene / 0.17 h / Heating View Scheme

1: 1.) (COCl)2, 2.) AlCl3 / 1.) CH2Cl2, RT, 1 h, 2.) CS2, reflux, 30 min 2: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 3: PTSA / benzene / 0.5 h / Heating 4: DDQ / benzene / 0.17 h / Heating View Scheme

1: Zn(Hg), HCl / acetic acid; toluene / 3 h / Heating 2: 1.) (COCl)2, 2.) AlCl3 / 1.) CH2Cl2, RT, 1 h, 2.) CS2, reflux, 30 min 3: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 4: PTSA / benzene / 0.5 h / Heating 5: DDQ / benzene / 0.17 h / Heating View Scheme