1: 94 percent / NaBH4 / tetrahydrofuran; methanol / 1 h / Ambient temperature 2: 100 percent / p-TsOH / benzene / Ambient temperature 3: o-chloranil / benzene / 72 h / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1: 1.) p-TsOH, 2.) 10percent KOH / 1.) benzene, RT, overnight, 2.) ethanediol, 185-190 deg C2: CH3SO3H / 4 h / 55 - 60 °C  

With  sodium tetrahydroborate in  tetrahydrofuran; methanol 1 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: 94 percent / NaBH4 / tetrahydrofuran; methanol / 1 h / Ambient temperature2: 100 percent / p-TsOH / benzene / Ambient temperature