1: 2N aq. KOH / benzene / 4 h / Heating 2: thionyl chloride / benzene / 3 h / Heating View Scheme

1: 2N aq. KOH / benzene / 4 h / Heating 2: thionyl chloride / benzene / 3 h / Heating 3: 77 percent / pyridine / 8 h / Heating View Scheme

diisobutylaluminium hydride in dichloromethane T=-78°C;

potassium hydroxide

1: 2N aq. KOH / benzene / 4 h / Heating 2: thionyl chloride / benzene / 3 h / Heating 3: 77 percent / pyridine / 8 h / Heating 4: 50 percent / boron tribromide / CH2Cl2 / 1)8h -80 deg C 2)3h room temp. View Scheme