1: 38 percent / NaH / toluene / 48 h / Heating 2: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 3: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

sodium hydride in toluene 48 h; Heating;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '11378922', constants.ctx, '0')">palladium on activated charcoal</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br />3&nbsp;h;&nbsp;&nbsp;Ambient temperature;&nbsp;<br /> &nbsp;