sodium ethanolate; sodium in ethanol

1: diethyl malonate With sodium hydride in 1,4-dioxane; mineral oil T=20°C; 2: 1-Bromo-2-benzyloxy-3-chloro-propane in 1,4-dioxane; mineral oil T=20°C; Reflux; 3: With sodium hydride in 1,4-dioxane; mineral oil Cooling with ice bathReflux;

T=125°C; 2 h;

2: sodium ethylate; benzene / 170 °C View Scheme

1,4-dioxane; sodium hydride

water; sodium chloride in dimethyl sulfoxide T=210°C; 48 h;

1: 92 percent / KOH / aq. ethanol / 1.5 h / Heating 2: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 3: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 4: 85 percent / H2 / PtO2 / methanol / 7 h View Scheme

potassium hydroxide in ethanol 1.5 h; Heating;

1: 92 percent / KOH / aq. ethanol / 1.5 h / Heating 2: 83 percent / 1. 150 deg C, 1 h, 4.0E3 Pa; 2. 165 deg C, 2.5 h; 3. 180 deg C, 2.5 h 3: 81 percent / H2SO4 / CHCl3 / 16 h / Heating 4: 85 percent / H2 / PtO2 / methanol / 7 h 5: 88 percent / pyridine / 336 h 6: 80 percent / NH4Br, NH3 / 144 h / Ambient temperature 7: 59 percent / NaN3 / methanol; H2O / 20 h / Heating 8: 81 percent / H2 / PtO2 / methanol / 6 h / Ambient temperature 9: 79 percent / HCl / H2O / 20 h / Heating View Scheme

palladium 10 on activated carbon; hydrogen in ethyl acetate T=20°C; P=760.051 Torr; 12 h;