1: 60 percent / H2 / Raney-Ni / ethanol; H2O / 48 h / 112509 - 150012 Torr / Ambient temperature 2: 91 percent / Et2O*BF3 / CH2Cl2 / 1.) 8 - 12 h, reflux; 2.) 24 h at room temp. 3: 96 percent / 2N KOH / ethanol / 1.) a few minutes heating to reflux; 2.) 0 deg C 4: SOCl2 / 0.5 h / Heating View Scheme

1: 91 percent / Et2O*BF3 / CH2Cl2 / 1.) 8 - 12 h, reflux; 2.) 24 h at room temp. 2: 96 percent / 2N KOH / ethanol / 1.) a few minutes heating to reflux; 2.) 0 deg C 3: SOCl2 / 0.5 h / Heating View Scheme

1: 96 percent / 2N KOH / ethanol / 1.) a few minutes heating to reflux; 2.) 0 deg C 2: SOCl2 / 0.5 h / Heating View Scheme