hydrogen; acetic acid; palladium on activated charcoal P=1520 - 2280 Torr; 1.5 h;

potassium hydroxide in tetrahydrofuran; methanol 2 h; Ambient temperature;

PPA; water in 1,4-dioxane Substitution; 25 h; Heating;

pyridine; chromium(VI) oxide in dichloromethane

1: NaBH4 / ethanol / Heating 2: (i) NaH, (ii) /BRN= 1098293/, (iii) /BRN= 969135/ 3: 210 - 235 °C 4: CrO3, Py / CH2Cl2 View Scheme

1: 1.) p-toluenesulfonic acid, 2.) O2, CuCl, PdCl2 / 1.) benzene, reflux, 20 h, 2.) aq. DMF, RT, 4.5 h 2: 88 percent / aq. KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature View Scheme

1: 85 percent / tetrabutylammonium hydrogen sulfate, aq. NaOH / 6 h / Ambient temperature 2: 91 percent / LiAlH4 / tetrahydrofuran / 2 h / 40 - 45 °C 3: 55 percent / Hg(OAc)2, H2SO4 / acetic acid; H2O / 3 h / Ambient temperature 4: 88 percent / aq. KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature View Scheme

1: 91 percent / LiAlH4 / tetrahydrofuran / 2 h / 40 - 45 °C 2: 55 percent / Hg(OAc)2, H2SO4 / acetic acid; H2O / 3 h / Ambient temperature 3: 88 percent / aq. KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature View Scheme

1: 55 percent / Hg(OAc)2, H2SO4 / acetic acid; H2O / 3 h / Ambient temperature 2: 88 percent / aq. KOH / tetrahydrofuran; methanol / 2 h / Ambient temperature View Scheme

2: 51 percent / POCl3, pyridine / 1.) 0 deg C, 15 min, 2.) 60-70 deg C, 2.5 h 3: benzene / 0.25 h / Irradiation; other solvents, var. conditions of irradiation, var. conc. of reactant 4: 100 percent / n-BuLi / tetrahydrofuran; hexane / 0.08 h View Scheme