1: 70 percent / di-isobutyl aluminiumhydride / tetrahydrofuran / 0 °C 2: 55 percent / DCC, dimethylaminopyridine / diethyl ether 3: 52 percent / AgO / dioxane; aq. HNO3 View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '393006', constants.ctx, '0')">chloranil</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8193445', constants.ctx, '0')">xylene</a> <br />T=150&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: K₂CO₃ / CHCl₃ <br />2: dichloroacetic acid<br />4: H₂ / Pd/C / methanol<br />5: 65 percent / chloranil / xylene / 150 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: dimethylsulfoxide<br />2: borane-THF<br />3: K₂CO₃ / CHCl₃ <br />4: dichloroacetic acid<br />6: H₂ / Pd/C / methanol<br />7: 65 percent / chloranil / xylene / 150 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: borane-THF<br />2: K₂CO₃ / CHCl₃ <br />3: dichloroacetic acid<br />5: H₂ / Pd/C / methanol<br />6: 65 percent / chloranil / xylene / 150 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: dichloroacetic acid<br />3: H₂ / Pd/C / methanol<br />4: 65 percent / chloranil / xylene / 150 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: H₂ / Pd/C / methanol<br />2: 65 percent / chloranil / xylene / 150 &deg;C<br /> <br /> &nbsp;