acetic acid T=70 - 100°C; 25 h; Product distribution / selectivity;

1: dichloromethane / 16 h / 20 °C 2: trifluoroacetic acid; formic acid / 5 h / 45 °C / Inert atmosphere View Scheme

<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, '11351177', constants.ctx, '0')">3 Pd/C</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=20&deg;C;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8402623', constants.ctx, '0')">sodium t-butanolate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=70 - 73&deg;C;&nbsp;15&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '506007', constants.ctx, '0')">acetic acid</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=60&deg;C;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '605351', constants.ctx, '0')">ethyl vinyl ether</a>; <a href="#" onclick="return RXDsubstances(event, this, '774355', constants.ctx, '0')">4-hydroxy-acetophenone</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '2037554', constants.ctx, '0')">sulfuric acid</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: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0 - 20&deg;C;&nbsp;pH=8;&nbsp;<br />Stage #3: <a href="#" onclick="return RXDsubstances(event, this, '1741905', constants.ctx, '0')">pentanoic acid methyl ester</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3556712', constants.ctx, '0')">potassium <i>tert</i>-butylate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1340512', constants.ctx, '0')">iso-butyronitrile</a> <br />T=0 - 95&deg;C;&nbsp;&nbsp;Product distribution / selectivity;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: sulfuric acid / tetrahydrofuran / 1.75 h / 0 &deg;C<br />2: potassium <i>tert</i>-butylate / iso-butyronitrile / 2 h / 0 - 95 &deg;C<br />3: water / hydrogenchloride / iso-butyronitrile / 0.25 h / 0 &deg;C<br /> <br /> &nbsp;