sodium hydroxide in ethanol 96 h; Heating;

1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / 0 °C 1.2: 14.0 g / hexane; tetrahydrofuran; various solvent(s) / 2 h / Heating 2.1: 6.7 g / dimethylsulfoxide / 2 h / 80 °C 3.1: Na2O2 / dimethylsulfoxide / 24 h / 20 °C 3.2: 67 percent / H2O / dimethylsulfoxide / 2 h / 80 °C View Scheme

1.1: 6.7 g / dimethylsulfoxide / 2 h / 80 °C 2.1: Na2O2 / dimethylsulfoxide / 24 h / 20 °C 2.2: 67 percent / H2O / dimethylsulfoxide / 2 h / 80 °C View Scheme

1: 1.) HMPT, n-BuLi / 1) THF, hexane, -20 deg C, 40 min; 2) 12 h, THF, hexane; 3) water, reflux, 48 h 2: 83 percent / NaOH / ethanol / 96 h / Heating View Scheme

Yield given. Multistep reaction;

(i) LiNH2, liq. NH3, THF, (ii) /BRN= 1745664/, THF; Multistep reaction;

(i) EtOH, (ii) NaOH; Multistep reaction;

hydrogen; Lindlar's catalyst