palladium 10 on activated carbon; hydrogen in ethyl acetate P=1551.49 Torr; 6 h;

1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, RT, 1 h 2: 89 percent / H2 / 10percent Pd/C / ethyl acetate 3: 39 percent / diphenyl ether / 2.75 h / 230 - 255 °C 4: 52 percent / DDQ / benzene / 2 h / Heating View Scheme