hydrogenchloride; hydrogen; palladium on activated charcoal 1) ethyl acetate, room temperature, atmospheric pressure, 2.) MeOH, reflux; Yield given. Multistep reaction;

1: 1.) NaH / 1.) benzene, reflux, 2.) room temperature 2: 1.) H2, 2.) aq. HCl / 1.) 10percent Pd/C / 1) ethyl acetate, room temperature, atmospheric pressure, 2.) MeOH, reflux View Scheme

1: 1.) NaH / 1.) DME, room temperature, 2.) 1 h 2: 1.) NaH / 1.) benzene, reflux, 2.) room temperature 3: 1.) H2, 2.) aq. HCl / 1.) 10percent Pd/C / 1) ethyl acetate, room temperature, atmospheric pressure, 2.) MeOH, reflux View Scheme