aluminum oxide in benzene 0.75 h; Heating;

1: 84 percent / zink dust, iodine / benzene; diethyl ether / 2 h / Heating 2: 1.) p-TsOH, 2.) 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) / 1.) benzene, reflux, 2h, 2.) reflux, 6h 3: 91 percent / KOH / H2O; methanol / 1 h / Heating 4: 84 percent / anhydrous HF / 15 h / Ambient temperature 5: NaBH4 / tetrahydrofuran; methanol 6: Al2O3 / benzene / 0.75 h / Heating View Scheme