1: With lithium aluminium tetrahydride in tetrahydrofuran Cooling with iceReflux; 2: With water in tetrahydrofuran Cooling with ice;

1: 85 percent / K2CO3 / H2O; CHCl3 / 4 h / Ambient temperature 2: 95 percent / K2CO3 / dimethylformamide / 4 h / 90 °C 3: 90 percent / 2N aq. NaOH / ethanol / Ambient temperature; overnight 4: PCl5 / 1,2-dichloro-ethane / 0.5 h / 60 °C 5: SnCl2 / 1,2-dichloro-ethane / 2 h / -10 °C 6: 85 percent / NaBH4 / ethanol / 1 h / Ambient temperature 7: pyrene, 0.1M tetrabutylammonium perchlorate / dimethylformamide / 0.5 h / cathode-mercury electrode, anode-graphite electrode; separation by membrane, ref. electrode-Ag/0.1M AgNO3, appl. pot.=-2.52 V View Scheme

1: 95 percent / K2CO3 / dimethylformamide / 4 h / 90 °C 2: 90 percent / 2N aq. NaOH / ethanol / Ambient temperature; overnight 3: PCl5 / 1,2-dichloro-ethane / 0.5 h / 60 °C 4: SnCl2 / 1,2-dichloro-ethane / 2 h / -10 °C 5: 85 percent / NaBH4 / ethanol / 1 h / Ambient temperature 6: pyrene, 0.1M tetrabutylammonium perchlorate / dimethylformamide / 0.5 h / cathode-mercury electrode, anode-graphite electrode; separation by membrane, ref. electrode-Ag/0.1M AgNO3, appl. pot.=-2.52 V View Scheme

hydrogenchloride; tin(ll) chloride in acetic acid T=65°C; 2 h; Yield given;