1.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2.1: NaBH4 / methanol / 1.5 h / 20 °C 3.1: 4.13 g / H2SO4 / 0.5 h / Heating 4.1: O3 / CH2Cl2 / -78 °C 4.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 5.1: 100 percent / NaOH / H2O / 2 h / 20 °C View Scheme

sodium hydroxide; dihydrogen peroxide in methanol 3 h; Ambient temperature;

1.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2.1: NaBH4 / methanol / 1.5 h / 20 °C 3.1: 4.13 g / H2SO4 / 0.5 h / Heating 4.1: O3 / CH2Cl2 / -78 °C 4.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 5.1: 100 percent / NaOH / H2O / 2 h / 20 °C 6.1: 68 percent / Fremy's salt; K2HPO4 / H2O; acetone / 1 h / 20 °C 7.1: 93 percent / NaOH / methanol; H2O / 0.25 h / 20 °C View Scheme

1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2: NaBH4 / methanol / 1.5 h / 20 °C 3: 4.13 g / H2SO4 / 0.5 h / Heating View Scheme

1.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2.1: NaBH4 / methanol / 1.5 h / 20 °C 3.1: 4.13 g / H2SO4 / 0.5 h / Heating 4.1: O3 / CH2Cl2 / -78 °C 4.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 5.1: 82 percent / CrO3; H2SO4 / H2O; acetone / 0.75 h / 20 °C 6.1: 68 percent / sulfuric acid / 1.25 h / Heating View Scheme

1.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2.1: NaBH4 / methanol / 1.5 h / 20 °C 3.1: 4.13 g / H2SO4 / 0.5 h / Heating 4.1: O3 / CH2Cl2 / -78 °C 4.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 5.1: 100 percent / NaOH / H2O / 2 h / 20 °C 6.1: 68 percent / Fremy's salt; K2HPO4 / H2O; acetone / 1 h / 20 °C View Scheme