1: 59 percent / NaI / acetone / 18 h 2: 41 percent / NaNO2 / dimethylsulfoxide / Heating 3: 45 percent / t-BuOK / 2-methyl-propan-2-ol / 16 h 4: NaOMe, TiCl3, aq. CH3COONH4 / methanol; tetrahydrofuran / 1 h 5: pyridine / tetrahydrofuran / 3.5 h 6: t-BuOK / benzene; 2-methyl-propan-2-ol / 2 h / Ambient temperature 7: 6 M HCl, glac. AcOH, O2 / 5 h / Heating View Scheme

1: 63 percent / p-TsOH / diethyl ether / 3 h / Ambient temperature 2: 59 percent / NaI / acetone / 18 h 3: 41 percent / NaNO2 / dimethylsulfoxide / Heating 4: 45 percent / t-BuOK / 2-methyl-propan-2-ol / 16 h 5: NaOMe, TiCl3, aq. CH3COONH4 / methanol; tetrahydrofuran / 1 h 6: pyridine / tetrahydrofuran / 3.5 h 7: t-BuOK / benzene; 2-methyl-propan-2-ol / 2 h / Ambient temperature 8: 6 M HCl, glac. AcOH, O2 / 5 h / Heating View Scheme

1: 41 percent / NaNO2 / dimethylsulfoxide / Heating 2: 45 percent / t-BuOK / 2-methyl-propan-2-ol / 16 h 3: NaOMe, TiCl3, aq. CH3COONH4 / methanol; tetrahydrofuran / 1 h 4: pyridine / tetrahydrofuran / 3.5 h 5: t-BuOK / benzene; 2-methyl-propan-2-ol / 2 h / Ambient temperature 6: 6 M HCl, glac. AcOH, O2 / 5 h / Heating View Scheme

1: 45 percent / t-BuOK / 2-methyl-propan-2-ol / 16 h 2: NaOMe, TiCl3, aq. CH3COONH4 / methanol; tetrahydrofuran / 1 h 3: pyridine / tetrahydrofuran / 3.5 h 4: t-BuOK / benzene; 2-methyl-propan-2-ol / 2 h / Ambient temperature 5: 6 M HCl, glac. AcOH, O2 / 5 h / Heating View Scheme

1: 1.) Cu(I)I / 1.) ether, -10 deg C, 2.) ether, 75 min, -10 deg C 2: 65 percent / 02, 6M HCl, acetic acid / 5 h / Heating View Scheme

hydrogenchloride; oxygen; acetic acid 5 h; Heating; Yield given;