1: sodium hydroxide / benzene / 20 h / 20 °C 2: 0.5 h / 200 °C / neat (no solvent, solid phase) 3: bromine; sodium sulfite / chloroform; water / 0 - 20 °C / Inert atmosphere View Scheme

1: sodium hydroxide / benzene / 20 h / 20 °C 2: 0.5 h / 200 °C / neat (no solvent, solid phase) View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;Metallation;&nbsp;0.5&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1699052', constants.ctx, '0')">boron triethoxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78 - 20&deg;C;&nbsp;Substitution;&nbsp;<br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=20&deg;C;&nbsp;Hydrolysis;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;