phenol T=125°C; 19 h;

1: 1.) 1-hydroxybenzotriazole, dicyclohexylcarbodiimide (DCC) / 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 8 h 2: HCl (gas) / diethyl ether / 0.5 h 3: H2 / 10percent Pd/C / ethanol / 1 h / 2068.6 Torr / Ambient temperature 4: 75 percent / LiAlH4 / tetrahydrofuran / Heating 5: 56 percent / phenol / 19 h / 125 °C View Scheme

1: HCl (gas) / diethyl ether / 0.5 h 2: H2 / 10percent Pd/C / ethanol / 1 h / 2068.6 Torr / Ambient temperature 3: 75 percent / LiAlH4 / tetrahydrofuran / Heating 4: 56 percent / phenol / 19 h / 125 °C View Scheme

1: H2 / 10percent Pd/C / ethanol / 1 h / 2068.6 Torr / Ambient temperature 2: 75 percent / LiAlH4 / tetrahydrofuran / Heating 3: 56 percent / phenol / 19 h / 125 °C View Scheme

1: 60 percent / tetrahydrofuran / Ambient temperature 2: 95 percent / HCl (gas) / diethyl ether / 1 h 3: 75 percent / LiAlH4 / tetrahydrofuran / Heating 4: 56 percent / phenol / 19 h / 125 °C View Scheme

1: 1.) triethylamine, ethyl chloroformate / 1.) THF, -10 deg C, 1.5 h, 2.) THF, RT, 3 h 2: 95 percent / HCl (gas) / diethyl ether / 1 h 3: 75 percent / LiAlH4 / tetrahydrofuran / Heating 4: 56 percent / phenol / 19 h / 125 °C View Scheme

1: 95 percent / HCl (gas) / diethyl ether / 1 h 2: 75 percent / LiAlH4 / tetrahydrofuran / Heating 3: 56 percent / phenol / 19 h / 125 °C View Scheme

1: 75 percent / LiAlH4 / tetrahydrofuran / Heating 2: 56 percent / phenol / 19 h / 125 °C View Scheme