(PhSO2)2 in dichloromethane-d2; toluene T=80°C; 21 h;

iodine in dichloromethane T=20°C; 1 h;

(PhSO2)2 in dichloromethane-d2; toluene T=80°C; 21 h;

1.1: (PhSO2)2 / toluene; CD2Cl2 / 21 h / 80 °C 2.1: NaH / tetrahydrofuran / 1 h / 0 °C 2.2: 82 percent / tetrahydrofuran / 5.5 h / 0 °C View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1902293', constants.ctx, '0')">(-)-menthol</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;1&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '', constants.ctx, '0')">Me₂C=CHCH₂-X</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605365', constants.ctx, '0')">N,N-dimethyl-formamide</a> <br />T=0 - 20&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: NaH / tetrahydrofuran / 1 h / 0 &deg;C<br />1.2: 86.2 percent / tetrahydrofuran / 0 &deg;C<br />2.1: (PhSO₂)2 / toluene; CD₂Cl₂ / 120 h / 80 &deg;C<br />2.2: H₂O / 80 &deg;C<br />3.1: NaH / tetrahydrofuran / 1 h / 0 &deg;C<br />3.2: 93.8 percent / tetrahydrofuran / 0 &deg;C<br /> <br /> &nbsp;