trifluoroacetic acid in dichloromethane T=0 - 20°C;

sodium hydroxide

1: <PhCH2NMe3>OH 2: aq. NaOH View Scheme

hydrogenchloride

1: KOAc/Ac2O / 2 h / Heating 2: 250 - 260 °C / 10 Torr 3: methanol 4: H2O/KOH / ethanol / 16 h / Ambient temperature 5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating 6: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 7: 92 percent / BF3*OEt2 / Ambient temperature 8: 94 percent / NaOMe / methanol / 2 h / Heating 9: 92 percent / SF4 / 24 h / Ambient temperature 10: 96 percent / H2O/KOH / ethanol / 16 h / Ambient temperature 11: 90 percent / diethyl ether; hexane / 2 h / Heating 12: 77 percent / m-chloroperbenzoic acid / CH2Cl2 / 72 h / Ambient temperature 13: 93 percent / NaOMe / methanol / 2 h / Heating 14: 81 percent / SF4 / 24 h / Ambient temperature View Scheme

1: KOAc/Ac2O / 2 h / Heating 2: 250 - 260 °C / 10 Torr 3: methanol 4: H2O/KOH / ethanol / 16 h / Ambient temperature 5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating 6: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 7: 92 percent / BF3*OEt2 / Ambient temperature 8: 94 percent / NaOMe / methanol / 2 h / Heating View Scheme

1: KOAc/Ac2O / 2 h / Heating 2: 250 - 260 °C / 10 Torr 3: methanol 4: H2O/KOH / ethanol / 16 h / Ambient temperature 5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating View Scheme

1: KOAc/Ac2O / 2 h / Heating 2: 250 - 260 °C / 10 Torr 3: methanol 4: H2O/KOH / ethanol / 16 h / Ambient temperature 5: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating 6: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 7: 92 percent / BF3*OEt2 / Ambient temperature 8: 94 percent / NaOMe / methanol / 2 h / Heating 9: 92 percent / SF4 / 24 h / Ambient temperature 10: 96 percent / H2O/KOH / ethanol / 16 h / Ambient temperature 11: thionyl chloride View Scheme