1: With acetic acid T=18 - 21°C; 0.583333 h; 2: With sodium hypochlorite in water 0.75 h;

hydrogenchloride in tetrahydrofuran

hydrogen; palladium on activated charcoal

1: 1.) t-BuOK / 1.) DME, from 0 deg C to RT, 2.) DME, RT 2: 100 percent / H2 / 10percent Pd/C / ethanol / 0.33 h / 108601 Torr / Ambient temperature 3: 90 percent / LAH / diethyl ether / -20 °C 4: 99 percent / aq. HCl / tetrahydrofuran View Scheme

1: With trimethylsilyl trifluoromethanesulfonate; diethylphosphinoethane in dichloromethane; toluene T=20°C; 1 h; Inert atmosphere; 2: With diisobutylaluminium hydride in hexane; dichloromethane; toluene T=0°C; 0.333333 h; Inert atmosphere; 3: With water; sodium hydrogencarbonate in methanol; hexane; dichloromethane; toluene T=40°C; 2 h; chemoselective reaction;

1: 1.) LDA, HMPA / 1.) THF, hexane, -45 deg C, 0.5 h; 2.) THF, hexane, -45 deg C, 1 h 2: LAH / tetrahydrofuran / 0.5 h / Ambient temperature 3: 1N HCl / tetrahydrofuran / 0.08 h / Ambient temperature 4: H2 / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature View Scheme

Yield given. Multistep reaction;

toluene-4-sulfonic acid in benzene Heating; Yield given;