sodium hydroxide; dihydrogen peroxide 1 h; Ambient temperature;

1: With water; sodium hydroxide in methanol; toluene T=0 - 5°C; pH=12; 2: With dihydrogen peroxide in methanol; water; toluene T=15°C; 3: With hydrogenchloride in methanol; water; toluene T=25 - 70°C; pH=< 2; Activated charcoal;

1: 100 percent / BH3 / tetrahydrofuran 2: 100 percent / SOCl2, pyridine 3: 99 percent / ethanol; H2O 4: 97 percent / H2SO4, HOAc / H2O 5: SOCl2 6: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 7: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 8: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 9: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: 100 percent / SOCl2, pyridine 2: 99 percent / ethanol; H2O 3: 97 percent / H2SO4, HOAc / H2O 4: SOCl2 5: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 6: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 7: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 8: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: SOCl2 2: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 3: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 4: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 5: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: 97 percent / H2SO4, HOAc / H2O 2: SOCl2 3: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 4: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 5: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 6: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O 3: SOCl2 4: Na2CO3 / toluene; H2O / 1.) 10 deg C, 0.5 h, 2.) RT, 1 h 5: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 6: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 7: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature 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

1: 83 percent / BH3 / tetrahydrofuran / 1.) reflux, 1h, 2.) overnight 2: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 3: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme

1: 1.) K, EtOH / 1.) Et2O, 10 min, 2.) Et2O, overnight 2: 80 percent / 2percent aq. NaOH, 30percent aq. H2O2 / 1 h / Ambient temperature View Scheme