1: 85 percent / toluene-p-sulphonic acid / benzene / 8 h / Heating 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 0.5 h / Heating; Irradiation View Scheme

1: 85 percent / toluene-p-sulphonic acid / benzene / 8 h / Heating 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 0.5 h / Heating; Irradiation 3: 88 percent / 20percent KOH / methanol / 24 h / Heating View Scheme

1: 85 percent / toluene-p-sulphonic acid / benzene / 8 h / Heating 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 0.5 h / Heating; Irradiation 3: 88 percent / 20percent KOH / methanol / 24 h / Heating 4: 1.) benzene, reflux, 6 h, 2) acid, reflux, 6h View Scheme

With  sodium tetrahydroborate in  methanol 16 h;  Ambient temperature;   

With  toluene-4-sulfonic acid in  benzene 8 h;  Heating;