sulfuric acid; acetic acid in water

1: 100 percent / SOCl2, pyridine 2: 99 percent / ethanol; H2O 3: 97 percent / H2SO4, HOAc / H2O View Scheme

1: 100 percent / BH3 / tetrahydrofuran 2: 100 percent / SOCl2, pyridine 3: 99 percent / ethanol; H2O 4: 97 percent / H2SO4, HOAc / H2O View Scheme

1: 99 percent / ethanol; H2O 2: 97 percent / H2SO4, HOAc / H2O View Scheme

1: H2SO4, CrO3 2: H2SO4 3: NaBH4 4: (i) PBr3, (ii) /BRN= 4652394/ 5: H2SO4 View Scheme

1: NaBH4 2: (i) PBr3, (ii) /BRN= 4652394/ 3: H2SO4 View Scheme

1: H2SO4 2: NaBH4 3: (i) PBr3, (ii) /BRN= 4652394/ 4: H2SO4 View Scheme

sodium hydroxide

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 6: 78 percent / H2 / 5percent Pd/C / ethanol / 5 h / 2585.7 Torr / Ambient temperature View Scheme

1: SOCl2 2: Na2CO3 / toluene; H2O / 1.5 h / 10 - 20 °C 3: 83 percent / borane/THF / 1 h / Heating View Scheme