sodium hydroxide in ethanol; water 4 h; Heating / reflux;

sulfuric acid

hydrogenchloride 30 h; Heating;

1: 68 percent / CH2Cl2 / 3 h / Ambient temperature 2: 22 percent / AlCl3 / 0.33 h / 100 - 120 °C 3: 1.) aq. NaOH, 2.) aq. H2O2 / 1.) RT, 30 min, 2.) 3.5 h View Scheme

1: 70 percent / K2CO3 / acetone / 60 h 2: 99.8 percent / 15 h / Heating 3: NaH / 1) 20 min at 0 deg C 2) reflux for 12 h 4: NaOH / 1) 1h reflux with NaOH 2) concentrated HCl 5: SOCl2 6: 1) ozone 2) dimethyl sulfide / 1) 3 in MeOH at -78 deg C 2) room temperature overnight 7: 57 percent / NaBH4 / ethanol / 3 h 8: 95 percent / pyridine / 24 h 9: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 10: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 11: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 12: 68 percent / 4.5M HCl / 30 h / Heating View Scheme

1: 99.8 percent / 15 h / Heating 2: NaH / 1) 20 min at 0 deg C 2) reflux for 12 h 3: NaOH / 1) 1h reflux with NaOH 2) concentrated HCl 4: SOCl2 5: 1) ozone 2) dimethyl sulfide / 1) 3 in MeOH at -78 deg C 2) room temperature overnight 6: 57 percent / NaBH4 / ethanol / 3 h 7: 95 percent / pyridine / 24 h 8: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 9: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 10: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 11: 68 percent / 4.5M HCl / 30 h / Heating View Scheme

1: SOCl2 2: 1) ozone 2) dimethyl sulfide / 1) 3 in MeOH at -78 deg C 2) room temperature overnight 3: 57 percent / NaBH4 / ethanol / 3 h 4: 95 percent / pyridine / 24 h 5: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 6: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 7: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 8: 68 percent / 4.5M HCl / 30 h / Heating View Scheme

1: NaOH / 1) 1h reflux with NaOH 2) concentrated HCl 2: SOCl2 3: 1) ozone 2) dimethyl sulfide / 1) 3 in MeOH at -78 deg C 2) room temperature overnight 4: 57 percent / NaBH4 / ethanol / 3 h 5: 95 percent / pyridine / 24 h 6: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 7: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 8: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 9: 68 percent / 4.5M HCl / 30 h / Heating View Scheme

1: 1) ozone 2) dimethyl sulfide / 1) 3 in MeOH at -78 deg C 2) room temperature overnight 2: 57 percent / NaBH4 / ethanol / 3 h 3: 95 percent / pyridine / 24 h 4: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 5: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 6: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 7: 68 percent / 4.5M HCl / 30 h / Heating View Scheme

1: 57 percent / NaBH4 / ethanol / 3 h 2: 95 percent / pyridine / 24 h 3: 63 percent / dimethylformamide / 13 h / 60 - 65 °C 4: 72 percent / hydrazine / 2-methyl-propan-2-ol / 3 h / Heating 5: 83.5 percent / diisopropylamine,n-BuLi / tetrahydrofuran / 1 h / -45 °C 6: 68 percent / 4.5M HCl / 30 h / Heating View Scheme