1: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 2: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 3: 95 percent / HNO3 / 0.02 h / 60 °C 4: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 5: 89 percent / CH3ONa / methanol / 1 h 7: 2 N HCl / 1 h View Scheme

1: 95 percent / conc. H2SO4 / 15 h / Heating 2: 80 percent / N-methylpyrrolidine / 0.5 h / Heating 3: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 4: 95 percent / HNO3 / 0.02 h / 60 °C 5: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 6: 89 percent / CH3ONa / methanol / 1 h 8: 2 N HCl / 1 h View Scheme

1: 95 percent / HNO3 / 0.02 h / 60 °C 2: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 3: 89 percent / CH3ONa / methanol / 1 h 5: 2 N HCl / 1 h View Scheme

1: 95 percent / 1) NaHCO3, CaI2, NaBH4; 2) CaI2, NaBH4 / tetrahydrofuran / 1) 0 to 5 deg C, 1 h; 2) room temp., 2 h 2: 95 percent / HNO3 / 0.02 h / 60 °C 3: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 4: 89 percent / CH3ONa / methanol / 1 h 6: 2 N HCl / 1 h View Scheme

1: 45 percent / CH3ONa / methanol / 1 h 2: 36 percent / 2) 20 percent NaCN / 1) quinoline, 3 h, reflux; 2) ligroin, 3 h 4: 2 N HCl / 1 h View Scheme

1: 71 percent / xylene / 2 h / Heating 2: 48 percent / CH3ONa / methanol / 1 h 4: 2 N HCl / 1 h View Scheme

1: 48 percent / CH3ONa / methanol / 1 h 3: 2 N HCl / 1 h View Scheme

1: 54 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 2: 97 percent / CH3ONa / methanol / 1 h 3: 36 percent / 2) 20 percent NaCN / 1) quinoline, 3 h, reflux; 2) ligroin, 3 h 5: 2 N HCl / 1 h View Scheme

1: 69 percent / 1) benzene, 90 min, reflux; 2) ethanol, 1 h 2: 89 percent / CH3ONa / methanol / 1 h 4: 2 N HCl / 1 h View Scheme

1: 97 percent / CH3ONa / methanol / 1 h 2: 36 percent / 2) 20 percent NaCN / 1) quinoline, 3 h, reflux; 2) ligroin, 3 h 4: 2 N HCl / 1 h View Scheme