1: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 2: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 3: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 4: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 5: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: Na2CO3 / toluene; H2O / 1.5 h / 10 - 20 °C 2: 83 percent / borane/THF / 1 h / Heating View Scheme

1: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 2: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 3: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 4: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

sodium carbonate in water; toluene T=10 - 20°C; 1.5 h; Yield given;

1: Na2CO3 / toluene; H2O / 1.5 h / 10 - 20 °C 2: 83 percent / borane/THF / 1 h / Heating 3: 1.) EtOK, 3.) H2O 4: aq. NaOH, H2O2 / 1 h / Ambient temperature View Scheme