1: 98 percent / Pd(Cl2)(CH3CN)2 / tetrahydrofuran / 4 h / 25 °C 2: 98 percent / LiAlH4 / diethyl ether / 2 h 3: 75 percent / 1.) sudan red, ozone; 2.) Me2S / CH2Cl2; methanol / 1.) -70 deg C, 5 h; 2.) to rt 4: 90 percent / O3 / CH2Cl2; methanol 5: LiAlH4 / tetrahydrofuran / Ambient temperature 6: 98 percent / 1.) NaH; 2.) tetrabutylammonium iodide / tetrahydrofuran / 2 h / Ambient temperature 7: 87 percent Spectr. / POCl3 / pyridine; CH2Cl2 / 48 h / -30 °C 8: 93 percent / sodium / diethyl ether; liquid ammonia / 0.67 h / -40 °C 9: 90 percent / pyridinium chlorochromate / CH2Cl2 / 1.25 h / Ambient temperature View Scheme

1.1: potassium hydroxide / ethanol; water / 24 h / 15 - 20 °C / |Inert atmosphere 2.1: sodium hydrogencarbonate / dimethyl sulfoxide / 6 h / 150 °C / |Inert atmosphere 3.1: ozone; sodium hydroxide / water; toluene / 0.58 h / -10 °C 4.1: potassium tert-butylate / tert-butyl alcohol / 0.83 h / |Inert atmosphere; |Reflux 4.2: 1 h / |Inert atmosphere; |Reflux 5.1: copper(ll) bromide; lithium bromide / acetonitrile / 20 h / |Inert atmosphere; |Reflux View Scheme

potassium hydroxide in ethanol; water T=15 - 20°C; 24 h; Inert atmosphere; chemoselective reaction;

1: 98 percent / Pd(Cl2)(CH3CN)2 / tetrahydrofuran / 4 h / 25 °C 2: 98 percent / LiAlH4 / diethyl ether / 2 h 3: 75 percent / 1.) sudan red, ozone; 2.) Me2S / CH2Cl2; methanol / 1.) -70 deg C, 5 h; 2.) to rt 4: 90 percent / O3 / CH2Cl2; methanol 5: LiAlH4 / tetrahydrofuran / Ambient temperature 6: 92 percent / ZnCl2 / 1,2-dichloro-ethane / 3 h View Scheme

1: potassium hydroxide / ethanol; water / 24 h / 15 - 20 °C / |Inert atmosphere 2: sodium hydrogencarbonate / dimethyl sulfoxide / 6 h / 150 °C / |Inert atmosphere View Scheme

With  dichloro bis(acetonitrile) palladium(II) in  tetrahydrofuran T=25°C; 4 h;   

Multi-step reaction with 2 steps 1: 50 percent / aq. KOH / ethanol; H2O / 70 h / 25 °C2: 35 percent / iodosobenzene diacetate, CaCO3, I2 / benzene / 2.5 h / Heating  

Multi-step reaction with 2 steps 1: 50 percent / aq. KOH / ethanol; H2O / 70 h / 25 °C2: 48 percent / iodosobenzene diacetate, CaCO3, I2 / benzene / 2.5 h / Heating  

Multi-step reaction with 2 steps 1: 50 percent / aq. KOH / ethanol; H2O / 70 h / 25 °C2: 76 percent / platinum oxide, NaNO2, H2 / ethanol / 2.5 h / 2068.6 Torr  

Multi-step reaction with 2 steps 1: 50 percent / aq. KOH / ethanol; H2O / 70 h / 25 °C2: 87 percent / vanadium(IV)-bis(2,4-pentanedionate) oxide, t-butyl hydroperoxide / CH2Cl2 / Heating; 1.) reflux, 2 h; 2.) 25 deg C, 1.5 h