toluene-4-sulfonic acid in benzene 0.75 h; Heating;

aluminum oxide in benzene 0.75 h; Heating;

1: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 2: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 3: 88 percent / aq. KOH / methanol / 1 h / Heating 4: 88 percent / anhydrous HF / 15 h / Ambient temperature 5: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 6: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

1: 70 percent / polyphosphoric acid / 3 h / 80 °C 2: 83 percent / zinc dust, iodine / benzene; diethyl ether / 1.) 15 min, reflux, 2.) 2h, reflux 3: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 4h 4: 88 percent / aq. KOH / methanol / 1 h / Heating 5: 88 percent / anhydrous HF / 15 h / Ambient temperature 6: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 7: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

1: 88 percent / dimethylsulfoxide / 2 h / 70 °C 2: 85 percent / KOH / ethane-1,2-diol; H2O / 24 h / Heating 3: anhydrous HF / 24 h / Ambient temperature 4: NaBH4 / tetrahydrofuran; methanol 5: Al2O3 / benzene / 0.75 h / Heating View Scheme

1: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 2: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

1: 85 percent / KOH / ethane-1,2-diol; H2O / 24 h / Heating 2: anhydrous HF / 24 h / Ambient temperature 3: NaBH4 / tetrahydrofuran; methanol 4: Al2O3 / benzene / 0.75 h / Heating View Scheme

1: anhydrous HF / 24 h / Ambient temperature 2: NaBH4 / tetrahydrofuran; methanol 3: Al2O3 / benzene / 0.75 h / Heating View Scheme

1: 88 percent / anhydrous HF / 15 h / Ambient temperature 2: 95 percent / Sodium borohydride / dimethylformamide / 6 h / Ambient temperature 3: 62 percent / p-TsOH / benzene / 0.75 h / Heating View Scheme

1: NaBH4 / tetrahydrofuran; methanol 2: Al2O3 / benzene / 0.75 h / Heating View Scheme