sodium hydroxide; water in methanol 20 h; Heating;

potassium hydroxide; ethanol

1: 100 percent / i-Bu2AlH / heptane / 1.) -78 deg C, 30 min, 2.) -78 deg C to room temperature, 3.5 h 2: 1.) n-BuLi, 3.) conc. HCl, 4.) aq. NaOH 3: 100 percent / Zn, AcOH / 24 h / Heating 4: 99 percent / ZnCl2 / acetic acid / 2 h / Heating 5: 99 percent / Na2Cr2O7*H2O / acetic acid / 1 h / Heating 7: 1.) HCl, 2.) NaBH4 / 2.) DMSO 8: 94 percent / HBr, HOAc / 3.5 h / Heating View Scheme

sodium cyanide in dimethyl sulfoxide T=160 - 170°C; 12 h; Yield given;

in dichloromethane

1: potassium hydroxide; propanol-(1) 2: aqueous hydrobromic acid; acetic acid View Scheme

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

palladium monocarbide in nitrobenzene

2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=60°C; 24 h; DDQ/substrate ratio = 3;

palladium monocarbide