sodium hydroxide in ethanol; water T=2 - 43°C; pH=12 - 12.5;

ozone in acetonitrile T=25°C; 24 h; Mechanism; SolventTemperature; regioselective reaction;

potassium 2-methylpropan-2-olate in tetrahydrofuran T=25°C; 16 h;

potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride in dichloromethane phase transfer oxidation; 6 h; Heating;

toluene

1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C View Scheme

sulfuric acid; nitric acid T=-10°C; 1 h;

1.1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2.1: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3.1: water / ethanol / 36 h / 60 °C / Industry scale 4.1: toluene / 3 h / Industry scale; Reflux 5.1: methylamine / ethanol / 4 h / 65 °C / Industry scale 5.2: 58 - 60 °C / pH 2.7 / Industry scale 6.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Industry scale 6.2: 2.5 h / 0 - 25 °C View Scheme

1: nitric acid; sulfuric acid / sulfolane / 2 h / -5 - 30 °C 2: hydrogen / Raney Ni / methanol / 24 h / 40 - 50 °C 3: water / ethanol / 36 h / 60 °C / Industry scale View Scheme