1.1: Mg / diethyl ether / 0.5 h / Heating 1.2: CdCl2 / diethyl ether / 0.75 h / Heating 1.3: 66 percent / toluene / 2 h / Heating 2.1: KOtBu / 2-methyl-propan-2-ol 2.2: 53 percent / HCl / tetrahydrofuran; H2O View Scheme

thionyl chloride

1: 99 percent / 0.75 h / 80 °C 2: 94 percent / SOCl2 View Scheme

benzene

1: 83 percent / SnCl4 / CH2Cl2 / 1.)0 deg C, 2.)R.T., 16 h 2: 90 percent / 85percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / Heating 3: 67 percent / Raney nickel, 10percent Na2CO3 / ethanol / 16 h / Heating 4: 96 percent / diethyl ether / 12 h / 0 °C 5: 1.)thallium(III) trifluoroacetate, trifluoracetic acid, 2.)isomayl nitrite, 12N HCl, AcOH / 1.)r.t., 48 h, 2.)CH2Cl2, red lights, 10 min. 6: 90 percent / NaBH4 / Palladium on charcoal / methanol / 0.5 h / Ambient temperature 7: 1.)0.5N HCl, sodium nitrite / 1.)0-5 deg C, 5 min., 2.)H2O, 0-5 deg C, 20 min. 8: 53 percent / 1N NaOH / ethanol / 1 h / Heating 9: 65 percent / Trifluoroacetic acid, NaI / acetone / 1.)0-5 deg C, 2.)15 min., 25 deg C View Scheme

1: 64 percent / AlCl3 / 2 h / Heating 2: 93 percent / KOH / methanol View Scheme

benzene

1: 85 percent / SnCl4 / CH2Cl2 / 3 h / 0 - 20 °C 2: 90 percent / KOH, 85percent hydrazine hydrate / various solvent(s) / 4 h / Heating 3: 63 percent / diethyl ether / 12 h / 0 - 5 °C 4: 66 percent / SnCl4 / CH2Cl2 / 3 h / 0 - 20 °C 5: 84 percent / KOH, 85percent hydrazine hydrate / various solvent(s) / 4 h / Heating 6: 1.) 10percent aq. Na2CO3, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, reflux, 18 h, 2.) EtOH, 40 psi, 18 h 7: 87 percent / NaI, chlorotrimethylsilane / acetonitrile / 18 h / Heating 8: 73 percent / hexamethylphosphoric acid triamide / 0.5 h / 0 °C 9: 80 percent / diethyl ether / 12 h / 0 - 5 °C 10: 1.) (n-Bu)3SnH, azobisbutyronitrile, 2.) iodine monochloride / 1.) toluene, reflux, 6 h, 2.) CCl4 11: 91 percent / 1 N aq. NaOH / ethanol / 1 h / Heating View Scheme