1: 49 percent / N-chlorosuccinimide / CCl4 / 15 h / Ambient temperature 2: methanol / 3 h / Heating 3: 66 percent / 10percent Pd/C / toluene / 15 h / 135 °C View Scheme

1: 49 percent / N-chlorosuccinimide / CCl4 / 15 h / Ambient temperature 2: 1.) MeONa, 2.) silica gel 60 / 1.) MeOH, reflux, 3 h, 2.) hexane, EtOAc 3: 88 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1: 49 percent / N-chlorosuccinimide / CCl4 / 15 h / Ambient temperature 2: methanol / 3 h / Heating View Scheme