Jones oxidant in acetone T=0°C; 0.416667 h;

sodium tetrahydroborate in ethanol Ambient temperature;

1: 80 percent / H2 / 5percent Pd/C / Ambient temperature 2: 75 percent / K2CO3 / H2O / 3 h / Ambient temperature 3: 73 percent / NaBH4 / ethanol / Ambient temperature View Scheme

1: benzene / 2 h / Heating 2: 73 percent / NaBH4 / ethanol / Ambient temperature View Scheme

1: 67 percent / HCl(g) 2: benzene / 2 h / Heating 3: 73 percent / NaBH4 / ethanol / Ambient temperature View Scheme

1: 75 percent / K2CO3 / H2O / 3 h / Ambient temperature 2: 73 percent / NaBH4 / ethanol / Ambient temperature View Scheme

in diethyl ether T=-5°C;

1: 56 percent / diethyl ether / 0.67 h / -5 °C 2: 81 percent / Hg(OAc)2 / 60 h / 200 °C / in a sealed tube 3: 77 percent / diethyl ether / 1 h / -5 °C 4: 68 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 9 h / Ambient temperature 5: 81 percent / p-TsOH / benzene / 8 h / Heating 6: 89 percent / B2H6 / tetrahydrofuran / 8 h / ice cooling 7: 80 percent / 1percent HCl / tetrahydrofuran / 1 h / Heating 8: 93 percent / Jones reagent / acetone / 2 h / ice cooling 9: 87 percent / anhyd. K2CO3 / ethanol / 2.5 h / Heating 10: 37 percent / LiAlH4 / diethyl ether / 1.) r.t., 5 h, 2.) reflux, 4 h View Scheme

1: 56 percent / diethyl ether / 0.67 h / -5 °C 2: 76 percent / Hg(OAc)2 / 72 h / 200 °C / in a sealed tube 3: 76 percent / diethyl ether / 2 h / -5 °C 4: 72 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 7 h / Ambient temperature 5: 92 percent / p-TsOH / benzene / 12 h / Heating 6: B2H6 / tetrahydrofuran / 3 h / ice cooling 7: 91 percent / 1percent HCl / tetrahydrofuran / 1 h / Heating 8: 87 percent / Jones reagent / acetone / 2 h / ice cooling 9: 88 percent / anhyd. K2CO3 / ethanol / 1.3 h / 45 - 50 °C 10: 37 percent / LiAlH4 / diethyl ether / 5.5 h / Ambient temperature View Scheme

triethylsilane; titanium tetrachloride in dichloromethane