1: benzene 2: n-BuLi / tetrahydrofuran; hexane View Scheme

potassium tert-butylate 1.) toluene, reflux, 15 min; 2.) toluene, -78 deg C, 30 min, 3.) toluene, 25 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

2: 79 percent / p-toluenesulfonic acid / ethanol / 1 h / Heating 3: 73 percent / KOH / ethanol / 1.5 h / Heating View Scheme

1: 76 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 95 percent / i-Pr2NEt / CH2Cl2 / 1 h / 0 °C 3: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 80 °C 4: 98 percent / pyridinium p-toluene sulfonate / ethanol / 8 h / 60 °C View Scheme

1: 1.)triphenylphosphine; 2.) zinc / 1.) dichloromethane, 10 min; 2.) 20 deg C, 24 h; 3.) dichloromethane, 25 deg C, 1h; 2: 80 percent / n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C View Scheme

1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine (DMAP) 2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C 3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C 4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C 5: 90 percent / DMAP, pyridine / 0.33 h / 0 °C View Scheme

1: 76 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 95 percent / i-Pr2NEt / CH2Cl2 / 1 h / 0 °C 3: 97 percent / LiAlH4 / tetrahydrofuran / 3 h / 80 °C 4: 98 percent / pyridinium p-toluene sulfonate / ethanol / 8 h / 60 °C 5: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Me3N / 1.) CH2Cl2, -78 deg C, 25 min, 2.) 1 h View Scheme

1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: tetrahydrofuran; hexane / 0 °C 2.1: PTSA / methanol / 1 h / 20 °C 3.1: 75 percent / Jones reagent / acetone / 0 - 20 °C 4.1: 60 percent / Li; liq. NH3 / tetrahydrofuran / 2 h / cooling View Scheme

1: 1.) HMPTA, n-BuLi, 3.) 4-dimethylaminopyridine (DMAP) 2: NaOH / diethyl ether; methanol / 0.33 h / 25 °C 3: Na2S2O4, NaHCO3 / ethanol; H2O / 7 h / 80 °C 4: 100 percent / TsOH*pyridine / methanol / 2 h / 50 °C 5: 1.) n-BuLi, Ph3CH, HMPTA, 2.) TsCl, 3.) NaBr 6: 1.) LDA, 2.) SiO2 / 1.) hexane, THF, HMPTA, 0 deg C, 45 min, 2.) hexane, THF, HMPTA. 0-25 deg C 7: 98 percent / LiAlH4 / diethyl ether / 0.17 h / 0 °C 8: 100 percent / ZnBr2, Me3SiBr / CH2Cl2 / 0.25 h / -20 °C 9: 89 percent / dibenzo-18-crown-6 (DB-18-C-6) / acetonitrile / 15 h / 80 °C View Scheme

1: With sodium dihydrogen phosphate dihydrate in water; acetonitrile T=-15°C; 0.166667 h; 2: With dihydrogen peroxide in water; acetonitrile 0.0833333 h; 3: With sodium chlorite in water; acetonitrile 1 h;