1: chromium(VI) oxide; acetic acid / 60 °C 2: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 2585.81 Torr 3: sodium hydroxide; methanol / 2 h / 20 °C 4: thionyl chloride / 1 h / 0 - 20 °C 5: pyridinium chlorochromate / dichloromethane / 20 °C 6: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme

1: chromium(VI) oxide; acetic acid / 60 °C 2: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 2585.81 Torr 3: sodium hydroxide; methanol / 2 h / 20 °C 4: thionyl chloride / 1 h / 0 - 20 °C 5: pyridinium chlorochromate / dichloromethane / 20 °C 6: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 20 °C / Inert atmosphere 7: water; lithium hydroxide hydrate / tetrahydrofuran / 20 °C View Scheme

1: chromium(VI) oxide; acetic acid / 60 °C 2: hydrogen / palladium 10 on activated carbon / ethyl acetate / 16 h / 2585.81 Torr 3: sodium hydroxide; methanol / 2 h / 20 °C View Scheme