hydrogen; platinum(IV) oxide in acetic acid P=2206.5 Torr;

1: K2CO3 / acetone / 18 h / Heating 2: 1 h / 200 °C 3: H2 / 5percent Pd/C / ethanol / 1551.4 Torr View Scheme

1: 1 h / 200 °C 2: H2 / 5percent Pd/C / ethanol / 1551.4 Torr View Scheme

1: 1.) EtONa, 2.) conc. HCl / 1.) ethanol, reflux, 2 h, 2.) ethanol, reflux, 15 h 2: 57 percent / ethanol / 17 h / Heating 3: 81 percent / diphenyl ether / 0.08 h / Heating 4: 59 percent / POCl3 / benzene / 25 h / Ambient temperature 5: 0.1 M NaOH / methanol / 0.25 h / Heating View Scheme