1: 1.) O3, 2.) acetic anhydride, sodium acetate, 3.) H2O; / 1.) cyclohexane, glacial acetic acid, 2.) glacial acetic acid, 3.) boiling; 2: 85 percent / diethyl ether / 0.03 h 3: 85 percent / tetrahydrofuran / 0.5 h / 0 °C 4: 85 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 5: CH3ONa / methanol / 0.33 h / 30 - 35 °C 6: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 7: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 8: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 9: conc. H2SO4 / benzene / 12 h / Heating View Scheme

1: 85 percent / diethyl ether / 0.03 h 2: 85 percent / tetrahydrofuran / 0.5 h / 0 °C 3: 85 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 4: CH3ONa / methanol / 0.33 h / 30 - 35 °C 5: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 6: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 7: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 8: conc. H2SO4 / benzene / 12 h / 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: 85 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 2: CH3ONa / methanol / 0.33 h / 30 - 35 °C 3: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 4: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 5: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 6: conc. H2SO4 / benzene / 12 h / Heating View Scheme

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

1: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 2: conc. H2SO4 / benzene / 12 h / Heating View Scheme

1: 1.) CH3ONa, 2.) H2SO4; / methanol / -5 °C 2: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 3: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 4: conc. H2SO4 / benzene / 12 h / Heating View Scheme

1: conc. HCl / propan-2-ol; CHCl3 / 1 h / Ambient temperature 2: 1percent aq. NaOH / ethanol / 0.25 h / 75 - 80 °C 3: conc. H2SO4 / benzene / 12 h / Heating View Scheme

sulfuric acid in benzene 12 h; Heating;