potassium hydroxide Heating;

1: H2 / Raney Ni / methanol / 20 °C 2: TsOH*H2O / toluene / Heating View Scheme

1: 54 percent / BBr3 / CH2Cl2 / 0.08 h / 0 °C 2: 87 percent / Ambient temperature; macroelectrolysis: mercury pool working electrode, tetraethylammonium p-toluenesulfonate supporting electrolyte View Scheme

1.1: potassium hydroxide / toluene / 1.5 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 5 h / -78 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 °C 4.1: tetrahydrofuran / 1 h / -78 °C View Scheme