1: 1.) Mg(OEt)2, CCl4 / 1.) EtOH, Et2O, reflux, 3 h, 2.) EtOH, Et2O, toluene, reflux, 3 h 2: 100 percent / 60percent aq. HOAc, H2SO4 / 7 h / Heating 3: 94 percent / H2 / 10percent Pd/C / methanol View Scheme

1: 1.) Mg(OEt)2, CCl4 / 1.) EtOH, Et2O, reflux, 3 h, 2.) EtOH, Et2O, toluene, reflux, 3 h 2: 100 percent / 60percent aq. HOAc, H2SO4 / 7 h / Heating 3: 94 percent / H2 / 10percent Pd/C / methanol 4: 95 percent / glacial acetic acid View Scheme

1: 1.) Mg(OEt)2, CCl4 / 1.) EtOH, Et2O, reflux, 3 h, 2.) EtOH, Et2O, toluene, reflux, 3 h 2: 100 percent / 60percent aq. HOAc, H2SO4 / 7 h / Heating View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209273', constants.ctx, '0')">thionyl chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1731042', constants.ctx, '0')">chloroform</a> <br />2&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 67 percent / KMnO₄ / acetone; H₂O / 20 h / 50 &deg;C<br />2: SOCl₂ / 3 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 83 percent / K₂CO₃ / acetone / 84 h / Heating<br />2: 67 percent / KMnO₄ / acetone; H₂O / 20 h / 50 &deg;C<br />3: SOCl₂ / 3 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 91 percent / aq. KOH / CH₂Cl₂ / overnight<br />2: 60 percent / 90percent HNO₃ / 0.5 h / -2 - 2 &deg;C<br />3: 95 percent / aq. NaOH / methanol / 0.5 h / Heating<br />4: 83 percent / K₂CO₃ / acetone / 84 h / Heating<br />5: 67 percent / KMnO₄ / acetone; H₂O / 20 h / 50 &deg;C<br />6: SOCl₂ / 3 h / Heating<br /> <br /> &nbsp;