DOWEX(R) 50WX8-200 ion-exchange resin; water 3 h; Heating;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3552389', constants.ctx, '0')">lithium methanolate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> <br />T=20&deg;C;&nbsp;14&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1: 1.) Et₃N, trimethylaluminum / 1.) CH₂Cl₂, RT, 15 min, 2.) CH₂Cl₂, reflux, 48 h<br />2: Jones reagent / acetone / 2 h / 0 - 20 &deg;C<br />3: benzene / 2.5 h / Heating<br />4: 83 percent / Et₄NOTS / methanol / anodic oxidation, carbon rod anode, Pt cathode<br />5: TiCl₄ / CH₂Cl₂ / 36 h / Ambient temperature<br />6: 1.) O₃, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h<br />7: 38 percent / Et₃N / benzene / 0 &deg;C<br />8: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating<br />9: 0.01 N HCl / methanol; H₂O / 2 h / 105 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 83 percent / Et₄NOTS / methanol / anodic oxidation, carbon rod anode, Pt cathode<br />2: TiCl₄ / CH₂Cl₂ / 36 h / Ambient temperature<br />3: 1.) O₃, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h<br />4: 38 percent / Et₃N / benzene / 0 &deg;C<br />5: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating<br />6: 0.01 N HCl / methanol; H₂O / 2 h / 105 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 10 steps<br /> </b>1: 1.) LDA / 1.) THF, hexane, -45 deg C, 1.5 h, 2.) THF, hexane, -45 deg C, 4.5 h<br />2: 1.) Et₃N, trimethylaluminum / 1.) CH₂Cl₂, RT, 15 min, 2.) CH₂Cl₂, reflux, 48 h<br />3: Jones reagent / acetone / 2 h / 0 - 20 &deg;C<br />4: benzene / 2.5 h / Heating<br />5: 83 percent / Et₄NOTS / methanol / anodic oxidation, carbon rod anode, Pt cathode<br />6: TiCl₄ / CH₂Cl₂ / 36 h / Ambient temperature<br />7: 1.) O₃, 2.) Zn-dust, HOAc / 1.) MeOH, -78 deg C, 0.5 h, 2.) MeOH, RT, 48 h<br />8: 38 percent / Et₃N / benzene / 0 &deg;C<br />9: 55 percent / 2,3-dichloro-4,5-dicyanobenzoquinone / dioxane / 3 h / Heating<br />10: 0.01 N HCl / methanol; H₂O / 2 h / 105 &deg;C<br /> <br /> &nbsp;