in methanol; hexane T=20°C; 2 h;

sodium methylate in methanol 2 h; Heating;

1: methanol 2: H2O/KOH / ethanol / 16 h / Ambient temperature 3: hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 10 h / Heating 4: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 5: 92 percent / BF3*OEt2 / Ambient temperature 6: 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 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: Raney-Ni / ethanol / Heating 2: KOH / aq. ethanol / Heating View Scheme

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

1: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 2: 92 percent / BF3*OEt2 / Ambient temperature 3: 94 percent / NaOMe / methanol / 2 h / Heating View Scheme

1: 92 percent / BF3*OEt2 / Ambient temperature 2: 94 percent / NaOMe / methanol / 2 h / Heating View Scheme

1: KOH / bis-(2-hydroxy-ethyl) ether / Heating 2: 91 percent / concn H2SO4 / 1,2-dichloro-ethane / 20 h / Heating 3: 92 percent / BF3*OEt2 / Ambient temperature 4: 94 percent / NaOMe / methanol / 2 h / Heating View Scheme

2: Py / Heating 3: 165 °C / 760000 Torr 4: H2 / Pd-C 5: aq. KOH 6: (i) AgNO3, aq. NaOH, (ii) Br2 7: NaOH View Scheme