triethylamine in benzene T=70°C; 2 h; Microwave irradiation;

potassium hydrogencarbonate in dichloromethane 48 h; Ambient temperature;

potassium hydroxide in ethanol 4 h; Ambient temperature;

1: 90 percent / aq. KOH / ethanol / 4 h / Ambient temperature 2: 61 percent / KOH / 96 h / Heating View Scheme

1: 90 percent / aq. KOH / ethanol / 4 h / Ambient temperature 2: 61 percent / KOH / 96 h / Heating 3: 67 percent / BH3 / tetrahydrofuran / 16 h / Heating 4: 70 percent / thionyl chloride / benzene / 24 h / Heating 5: 1.) NaH / 1.) EtOH, 10 min, 2.) EtOH, reflux, 24 h 6: 93 percent / 48percent HBr / 5 h / 130 - 140 °C View Scheme

1: 90 percent / aq. KOH / ethanol / 4 h / Ambient temperature 2: 61 percent / KOH / 96 h / Heating 3: 67 percent / BH3 / tetrahydrofuran / 16 h / Heating 4: 70 percent / thionyl chloride / benzene / 24 h / Heating View Scheme