The Heck reaction in ionic liquids: A multiphasic catalyst system

Organic Letters

Volumn 1, Issue 7, 1999, Pages 997-1000

  Carmichael, Adrian J ^a   Earle, Martyn J ^a   Holbrey, John D ^a   McCormac, Paul B ^a   Seddon, Kenneth R ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001322053     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9907771     Document Type: Article

References (35)

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22. 3), followed by decanting off a hexane solution of the product. This was repeated three further times. The combined hexane extracts were concentrated on a rotary evaporator, and the product was purified by Kugelrohr distillation. This gave 1.67 g of a colorless oil (yield = 95%). The spectroscopic properties of this oil were in accordance with those of authentic trans-ethyl cinnamate.
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25. 6] at 70°C. For background information of this reaction, see: Herrmann, W. A.; Bohn, V. P. W. J. Organomet. Chem. 1999, 572, 141.
26. The reaction was carried out six times without loss of activity of the catalyst. The product (trans-ethyl cinnamate) was extracted from the reaction vessel with cyclohexane, and the triethylammonium iodide salt was removed by solvent extraction with water. It is important to note that this reaction will work in the presence of a very large excess of water (a 50-fold excess does not hinder this reaction).
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31. Owing to the high reaction temperatures (above the boiling point of butyl acrylate), the reaction was carried out in a sealed thick walled glass reaction vessel.
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35. 2 mol % of ligand was added (4 mol % in P atoms).