sulfuric acid; mercury(II) oxide in tetrahydrofuran 5 h; Heating;

aluminium trichloride; sodium chloride T=190°C; 0.166667 h;

1: 50 percent / AlCl3-NaCl / neat (no solvent) / 0.17 h / 180 °C 2: 96 percent / hydrogen / Pd/C / ethyl acetate / 1 h / 25 °C 3: PTS acid 4: epoxydation 5: 1) base, 2) acid View Scheme

1: 96 percent / hydrogen / Pd/C / ethyl acetate / 1 h / 25 °C 2: PTS acid 3: epoxydation 4: 1) base, 2) acid View Scheme

1: 50 percent / AlCl3-NaCl / neat (no solvent) / 0.17 h / 180 °C 2: 96 percent / hydrogen / Pd/C / ethyl acetate / 1 h / 25 °C 3: PTS acid 4: epoxydation 5: 1) base, 2) acid View Scheme

1: PTS acid / benzene / 6 h / Heating 2: H2NNH2*H2O, KOH / 4 h / 160 - 165 °C 3: H(1+) 4: 50 percent / AlCl3-NaCl / neat (no solvent) / 0.17 h / 180 °C 5: 96 percent / hydrogen / Pd/C / ethyl acetate / 1 h / 25 °C 6: PTS acid 7: epoxydation 8: 1) base, 2) acid View Scheme

1: 66 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 2: 88 percent / HgO(yellow), 20percent H2SO4 / tetrahydrofuran / 5 h / Heating View Scheme

1: 89 percent / CeCl3, n-BuLi / tetrahydrofuran / 2 h / -78 °C 2: 71 percent / NaOEt / ethanol / 0.83 h / Ambient temperature 3: 85 percent / KOH / ethanol; H2O / 1 h / Heating 4: 99 percent / (trimethylsilyl)ethoxyacetylene 5: 66 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 6: 88 percent / HgO(yellow), 20percent H2SO4 / tetrahydrofuran / 5 h / Heating View Scheme

1: 99 percent / (trimethylsilyl)ethoxyacetylene 2: 66 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 3: 88 percent / HgO(yellow), 20percent H2SO4 / tetrahydrofuran / 5 h / Heating View Scheme

1: 85 percent / KOH / ethanol; H2O / 1 h / Heating 2: 99 percent / (trimethylsilyl)ethoxyacetylene 3: 66 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 4: 88 percent / HgO(yellow), 20percent H2SO4 / tetrahydrofuran / 5 h / Heating View Scheme