manganese(IV) oxide in chloroform 48 h; Ambient temperature;

lithium aluminium tetrahydride in tetrahydrofuran T=-15°C; 1.5 h; Inert atmosphere;

trifluoroacetic acid in dichloromethane Decarboxylation;

1: 70 percent / Br2, 10percent aq. NaOH / 0.17 h / 80 °C 2: 65 percent / conc. H2SO4 / benzene / 24 h / 90 °C 3: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 5 °C 4: 92 percent / MnO2 / CHCl3 / 48 h / Ambient temperature View Scheme

1: 65 percent / conc. H2SO4 / benzene / 24 h / 90 °C 2: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 5 °C 3: 92 percent / MnO2 / CHCl3 / 48 h / Ambient temperature View Scheme

1: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 5 °C 2: 92 percent / MnO2 / CHCl3 / 48 h / Ambient temperature View Scheme

1.1: dinitrogen pentaoxide; sodium hydrogensulfite / methanol; nitromethane; water / 0 °C / Inert atmosphere 2.1: sodium dithionite; ethanol / 6 h / Reflux; Inert atmosphere 3.1: Me2AlCl / hexane; dichloromethane / 150 h / 0 - 20 °C / Inert atmosphere 3.2: 20 h / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -15 °C / Inert atmosphere View Scheme

1.1: Me2AlCl / hexane; dichloromethane / 150 h / 0 - 20 °C / Inert atmosphere 1.2: 20 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -15 °C / Inert atmosphere View Scheme

1.1: sodium dithionite; ethanol / 6 h / Reflux; Inert atmosphere 2.1: Me2AlCl / hexane; dichloromethane / 150 h / 0 - 20 °C / Inert atmosphere 2.2: 20 h / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / -15 °C / Inert atmosphere View Scheme

sodium hydroxide in water Condensation;