1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C View Scheme

1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C 3: sodium wire / diethyl ether / 18 h / Ambient temperature 4: ethanol / 7 h / Heating 5: 59 percent / NaOH / H2O; ethanol / 60 °C View Scheme

sulfuric acid

1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C 3: NaH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature View Scheme

1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C 3: NaH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature 4: sodium methoxide / methanol / 18 h / Heating View Scheme

1: conc. H2SO4 2: H2 / 5percent Pd/C / ethanol / 45 °C 3: NaH / 1,2-dimethoxy-ethane / 20 h / Ambient temperature 4: sodium methoxide / methanol / 18 h / Heating 5: 67 percent / 2.) ethanolic hydrogen chloride / ethanol / 24 h / Heating View Scheme