potassium hydroxide in 1,4-dioxane T=50°C; 120 h;

potassium hydroxide in 1,4-dioxane; ethylene glycol T=50°C; 120 h;

cesium hydroxide; p-toluenesulfonyl chloride in 1,4-dioxane

1: 92 percent / NaI / acetone / Heating 2: 95 percent / K2CO3 / acetone / 72 h / Ambient temperature 3: 60 percent / KOH / tetrahydrofuran; H2O / 2 h / 0 °C 4: 13 percent / KOH / dioxane; ethane-1,2-diol / 120 h / 50 °C View Scheme

1: 95 percent / K2CO3 / acetone / 72 h / Ambient temperature 2: 60 percent / KOH / tetrahydrofuran; H2O / 2 h / 0 °C 3: 13 percent / KOH / dioxane; ethane-1,2-diol / 120 h / 50 °C View Scheme

1: NaOH / butan-1-ol / 30 h / Heating 2: conc. HCl / CH2Cl2; methanol / 1 h / Ambient temperature 3: 59 percent / CsOH, p-toluenesulfonyl chloride / dioxane View Scheme