sodium hydroxide in acetonitrile 1 h; Heating;

1.1: 92 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - 20 °C 2.2: 57 percent / tetrahydrofuran; hexane / 0.33 h View Scheme

1: 10.80 g / NaOH / H2O / 3 h / Heating 2: oxalyl chloride / CH2Cl2 / 24 h / 20 °C 3: Et3N / 1,2-dichloro-ethane / 20 °C 4: 1.027 g / SOCl2 / CH2Cl2; benzene / 4 h / 20 °C 5: 75 percent / diethyl ether / 24 h / 20 °C 6: 20 °C 7: NaOH / methanol; H2O / 12 h / Heating 8: 0.340 g / H2SO4 / 0.08 h / 20 °C 9: 66 percent / HBr; AcOH / 5 h / Heating View Scheme

ammonium cerium(IV) nitrate in acetonitrile T=0°C; 0.333333 h;