1: 2.) dilute aq. HCl; / 1.) benzene, boiling, 10 h, 2.) 40 deg C, 15 min; 3.) room temperature, 2 h; 2: 90 percent / conc. HCl / 5 h / 90 °C View Scheme

1: 2.) dilute aq. HCl; / 1.) benzene, boiling, 10 h, 2.) 40 deg C, 15 min; 3.) room temperature, 2 h; 2: conc. HCl / Heating View Scheme

1: 85 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 85 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 3: CH3ONa / methanol / 0.33 h / 30 - 35 °C 4: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 5: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 6: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 7: conc. H2SO4 / benzene / 12 h / Heating View Scheme

1: 95 percent / (Ph3P)3RhCl / CH2Cl2 / 18 h / Ambient temperature 2: 75 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 3: 85 percent / triphenylphosphine, bromine / CCl4 / 15 °C View Scheme