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[C4mim][OH] T=25 - 30°C; Knoevenagel condensation; 2 h;

ethanol; sodium 1.) 15 min, reflux, 2.) overnight; Yield given. Multistep reaction;

hydrogenchloride in hexane; water

1: aq. ethanol 2: (i) (hydrolysis), (ii) (decarboxylation) View Scheme

1: 1.) Na, C2H5OH / 1.) 15 min, reflux, 2.) overnight 2: 91 percent / conc. H2SO4, H2O / 24 h / Heating 3: 80 percent / H2SO4 / toluene / 24 h / Heating 4: 70 percent / sodium / toluene / 28 h / Heating 5: 70 percent / 85 percent phosphoric acid / 1.42 h / 100 - 170 °C / 20 - 40 Torr 6: 93 percent / LiAlH4 / diethyl ether / 22 h / Heating 7: 48 percent aq. HBr, conc. sulfuric acid / 48 h / 25 °C 8: 58 percent / quinoline / 150 - 195 °C View Scheme

ethanol; sodium ethanolate T=-10 - -5°C; und folgenden schnellen Erhitzen mit Methyljodid und Kochen;