hydrogen; palladium on activated charcoal in methanol; acetone T=50°C; 1 h;

<b>Multi-step reaction with 5 steps<br /> </b>1: 12 percent / CuCl, K₂CO₃ / 2-ethoxy-ethanol / 6 h / Heating<br />2: 59 percent / polyphosphoric acid (PPA) / 1 h / 115 &deg;C<br />3: 66 percent / K₂CO₃ / propan-2-ol / 2 h / Heating<br />4: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />5: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 66 percent / K₂CO₃ / propan-2-ol / 2 h / Heating<br />2: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />3: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />2: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 1.) sec-BuLi, TMEDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min<br />2: 81 percent / K₂CO₃, CuCl / propan-2-ol / 1.5 h / Heating<br />3: 69 percent / K₂CO₃ / dimethylformamide / 3 h / 20 - 45 &deg;C<br />4: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h<br />5: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />6: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 59 percent / polyphosphoric acid (PPA) / 1 h / 115 &deg;C<br />2: 66 percent / K₂CO₃ / propan-2-ol / 2 h / Heating<br />3: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />4: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 4 N aq. NaOH / benzene; CH₂Cl₂; H₂O / 1 h / Ambient temperature<br />2: 1.) sec-BuLi, TMEDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min<br />3: 81 percent / K₂CO₃, CuCl / propan-2-ol / 1.5 h / Heating<br />4: 69 percent / K₂CO₃ / dimethylformamide / 3 h / 20 - 45 &deg;C<br />5: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h<br />6: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />7: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 66 percent / K₂CO₃ / propan-2-ol / 2 h / Heating<br />2: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature<br />3: 48 percent / 6 N aq. HCl / ethanol / 4 h / Heating<br /> <br /> &nbsp;