1: 82 percent / 70percent HCl / 3 h / 10 °C 2: 58 percent / KMnO4, 20percent KOH / acetone; H2O / 1 h / 10 °C 3: 78 percent / diethyl ether / 0 - 5 °C 4: 1.) 2N BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) 1 h View Scheme

1: 78 percent / diethyl ether / 0 - 5 °C 2: 1.) 2N BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) 1 h View Scheme

1: 58 percent / KMnO4, 20percent KOH / acetone; H2O / 1 h / 10 °C 2: 78 percent / diethyl ether / 0 - 5 °C 3: 1.) 2N BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) 1 h View Scheme

n-butyllithium 1.) THF, hexane, -78 deg C, 10 min, 2.) 1 h; Yield given. Multistep reaction;