1: NBS / CCl4 / 6 h / Heating; Irradiation 2: 1 h / 180 °C / 10 Torr 3: 68.6 percent / H2, Ca(OH)2 / 10percent Pd/C / dioxane / 48 h / 2068.6 Torr 4: 1.) NBS, benzoyl peroxide, 2.) H2O / 1.) CCl4, reflux, 1 h, 2.) reflux View Scheme

1: 1 h / 180 °C / 10 Torr 2: 68.6 percent / H2, Ca(OH)2 / 10percent Pd/C / dioxane / 48 h / 2068.6 Torr 3: 1.) NBS, benzoyl peroxide, 2.) H2O / 1.) CCl4, reflux, 1 h, 2.) reflux View Scheme

1: 68.6 percent / H2, Ca(OH)2 / 10percent Pd/C / dioxane / 48 h / 2068.6 Torr 2: 1.) NBS, benzoyl peroxide, 2.) H2O / 1.) CCl4, reflux, 1 h, 2.) reflux View Scheme

potassium carbonate in methanol

N-bromosuccinmide; meta-chloroperoxybenzoic acid; water 1.) CCl4, reflux, 1 h, 2.) reflux; Yield given. Multistep reaction. Yields of byproduct given;