hydrogen; palladium on activated charcoal in ethanol P=3620.04 Torr; 10 h;

1: 86 percent / NaOH / ethanol; H2O / 5 h / Heating 2: 1) sec-BuLi / 1) THF, hexane, -78 deg C, 2) -78 deg C to room temperature 3: 95 percent / SOCl2 / benzene / Heating 4: 58 percent / CsF / acetonitrile / 5 h / Heating 5: 94 percent / lithium aluminum hydride / diethyl ether / 2 h / Heating View Scheme