sodium hydroxide in methanol 4 h; Heating;

1: bromine; sodium acetate / acetic acid / 20 - 115 °C 2: potassium permanganate; sodium hydroxide / water / 3 h / 100 °C View Scheme

1: 43 percent / Br2; NaOAc; acetic acid / 115 °C 2: 100 percent / aq. NaOH / methanol / 4 h / Heating View Scheme

1.1: hydrazine hydrate / butan-1-ol / Reflux 2.1: sodium hydroxide; water; potassium permanganate / 80 - 90 °C 3.1: sulfuric acid / 6 h / Reflux; Inert atmosphere 4.1: sodium acetate; bromine; acetic acid / 120 °C / in a sealed tube 5.1: sodium hydroxide; water / 3 h / 90 °C 5.2: 0 °C View Scheme

1.1: lithium diisopropyl amide / hexane; tetrahydrofuran; ethylbenzene / 3 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - -40 °C 1.3: -40 - -10 °C 2.1: chromium(VI) oxide / acetone / 3.25 h / -30 - 20 °C / Inert atmosphere 3.1: hydrazine hydrate / butan-1-ol / Reflux 4.1: sodium hydroxide; water; potassium permanganate / 80 - 90 °C 5.1: sulfuric acid / 6 h / Reflux; Inert atmosphere 6.1: sodium acetate; bromine; acetic acid / 120 °C / in a sealed tube 7.1: sodium hydroxide; water / 3 h / 90 °C 7.2: 0 °C View Scheme

1.1: chromium(VI) oxide / acetone / 3.25 h / -30 - 20 °C / Inert atmosphere 2.1: hydrazine hydrate / butan-1-ol / Reflux 3.1: sodium hydroxide; water; potassium permanganate / 80 - 90 °C 4.1: sulfuric acid / 6 h / Reflux; Inert atmosphere 5.1: sodium acetate; bromine; acetic acid / 120 °C / in a sealed tube 6.1: sodium hydroxide; water / 3 h / 90 °C 6.2: 0 °C View Scheme

1.1: sulfuric acid / 6 h / Reflux; Inert atmosphere 2.1: sodium acetate; bromine; acetic acid / 120 °C / in a sealed tube 3.1: sodium hydroxide; water / 3 h / 90 °C 3.2: 0 °C View Scheme

sulfuric acid T=70°C; 20 h; Large scale;