1: 1.) potassium / 1.) toluene, 90 deg C, 2.) reflux, 15 h 2: NaOH / ethanol; H2O / 1 h / Heating 3: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight 4: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 5: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: 1.) potassium / 1.) toluene, 90 deg C, 2.) reflux, 15 h 2: NaOH / ethanol; H2O / 1 h / Heating 3: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight View Scheme