1: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 2: PPE / CH2Cl2 / 0.5 h / Heating 3: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 4: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating 5: 95 percent / 150 - 215 °C 6: 87 percent / KOH / acetone / Ambient temperature View Scheme

1: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 2: PPE / CH2Cl2 / 0.5 h / Heating 3: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h View Scheme

1: H2 / 10percentPd-C / acetic acid; aq. HClO4 / 4 h / 60 °C / 2585.7 Torr 2: PPE / CH2Cl2 / 0.5 h / Heating 3: 1.) H2SO4, 2.) o-chloranil / 1.) toluene, reflux, 2h, 2.) reflux, 1h 4: 96 percent / NaBH4 / 1,2-dimethoxy-ethane / 3 h / Heating View Scheme