N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 0.5 h; HeatingIrradiation;

1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 0.5 h / Heating; Irradiation 2: 88 percent / 20percent KOH / methanol / 24 h / Heating View Scheme

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

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

Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 16 h / Ambient temperature2: 85 percent / toluene-p-sulphonic acid / benzene / 8 h / Heating