1: 99.8 percent / NaBH4 / methanol / 0.17 h 2: 94 percent / conc. HCl / methanol / 1 h / 20 °C View Scheme

1: 77 percent / H2SO4/SiO2 / toluene / 1 h / Heating 2: 92 percent / H2SO4/SiO2, water / toluene / 2 h 3: 89 percent / H2SO4/SiO2, EtOH / 2 h / Ambient temperature View Scheme

1: 75 percent / t-BuLi / tetrahydrofuran / 1) -70 deg C, 15 min, 2) -10 deg C, 2h 2: LiAlH4 / tetrahydrofuran View Scheme

1: 77 percent / H2SO4/SiO2 / toluene / 1 h / Heating 2: 92 percent / H2SO4/SiO2, water / toluene / 2 h View Scheme

1: 1.) t-BuLi / 1.) diethyl ether, pentane, -78 deg C, 1 h, 2.) diethyl ether, pentane, THF, -78 deg C, 11 h 2: 21 percent / Jones' reagent / acetone / 0.67 h / 0 °C 3: 70 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / toluene / 5 h / 100 °C View Scheme