2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 1 h; Heating;

1: 96 percent / Na2Cr2O7 / H2O / 6 h / 250 °C 2: 1) 20percent aq. NH3, Zn, CuSO4, 2) Li2CO3 / 1) 4 h, reflux, 2) DMF, 18 h, 20 deg C View Scheme

1: 1) 20percent aq. NH3, Zn, CuSO4, 2) Li2CO3 / 1) 4 h, reflux, 2) DMF, 18 h, 20 deg C 2: 91 percent / DDQ / benzene / 1 h / Heating View Scheme

1: 1) hydrochinone, 2) 5percent KOH / 1) C2H5OH, 6 h, 130 deg C, 2) C2H5OH, 8 h, 40-50 deg C; 12 h, RT 2: 96 percent / Na2Cr2O7 / H2O / 6 h / 250 °C 3: 1) 20percent aq. NH3, Zn, CuSO4, 2) Li2CO3 / 1) 4 h, reflux, 2) DMF, 18 h, 20 deg C View Scheme

ammonium hydroxide; lithium carbonate; copper(II) sulfate; zinc 1) 4 h, reflux, 2) DMF, 18 h, 20 deg C; Yield given. Multistep reaction. Yields of byproduct given;

1: 97 percent / LiAlH4 / tetrahydrofuran / 24 h 2: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme