1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=15 - 20°C;

1.1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2.1: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 3.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 4.1: ammonia / toluene / 0 - 5 °C / pH 10 - 11 5.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C 6.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr 6.2: 1 h / 50 - 55 °C 7.1: sodium hydroxide / water; toluene / 0.25 h / 20 - 25 °C 7.2: 35 - 40 °C View Scheme

1.1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2.1: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 3.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 4.1: ammonia / toluene / 0 - 5 °C / pH 10 - 11 5.1: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C 6.1: sodium hydroxide; hydrogen / water; methanol; isopropyl alcohol / 25 - 30 °C / 7500.75 Torr 6.2: 1 h / 50 - 55 °C View Scheme

1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 3: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 4: ammonia / toluene / 0 - 5 °C / pH 10 - 11 View Scheme

1: potassium hydroxide / tert-butyl alcohol / 2 h / 85 - 90 °C 2: palladium on activated charcoal; sodium carbonate; acrylic acid / water / 100 - 105 °C 3: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 35 - 40 °C 4: ammonia / toluene / 0 - 5 °C / pH 10 - 11 5: trichlorophosphate / dichloromethane; N,N-dimethyl-formamide / 2 h / 85 °C View Scheme