1: 42 percent / ethanol / 17 h / Heating 2: 67 percent / 0.17 h / 100 °C 3: 95 percent / toluenesulfonic acid / xylene / 0.25 h / Heating 4: 1) NBS, 2) p-TsOH / 1) EtOH, 35 deg C, 2) Xylene, reflux 5: 59 percent / NBS / H2O; acetone View Scheme

1: 42 percent / ethanol / 17 h / Heating 2: 67 percent / 0.17 h / 100 °C 3: 95 percent / toluenesulfonic acid / xylene / 0.25 h / Heating 4: NBS / H2O; acetone 5: 90 percent / NaH / tetrahydrofuran / 0.33 h / 25 °C 6: MCPBA / CH2Cl2 / 1) -78 deg C, 2) 25 deg C 7: 53 percent / 4 h / 110 °C 8: 51 percent / Cu(OAc)2*H2O / 1 h / Heating View Scheme

acetic anhydride