1: HIO4 / tetrahydrofuran; H2O / 25 °C 2: 92 percent / AcOOH; NaOAc / ethyl acetate / 20 h / 20 °C 3: 49 percent / aq. H2O2; aq. H2SO4 / ethyl acetate / 20 h / 20 °C View Scheme

1: 90 percent / O3 / CH2Cl2; methanol 2: LiAlH4 / tetrahydrofuran / Ambient temperature 3: 98 percent / 1.) NaH; 2.) tetrabutylammonium iodide / tetrahydrofuran / 2 h / Ambient temperature 4: 87 percent Spectr. / POCl3 / pyridine; CH2Cl2 / 48 h / -30 °C 5: 93 percent / sodium / diethyl ether; liquid ammonia / 0.67 h / -40 °C 6: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.25 h / Ambient temperature View Scheme

1: O3; pyridine / CH2Cl2 / -78 °C 2: 72 mg / LiAlH4 / tetrahydrofuran / 0 - 20 °C 3: 87 percent / p-toluenesulfonic acid / nitromethane / 3 h / 20 °C View Scheme

3-chloro-benzenecarboperoxoic acid in dichloromethane T=0°C; Baeyer-Villiger oxidation; 0.5 h; Darkness;

peracetic acid; sodium acetate in dichloromethane; acetic acid T=0 - 20°C; 1.5 h;