Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions

Organic Letters

Volumn 6, Issue 5, 2004, Pages 707-710

  Earle, Martyn J ^a   Katdare, Suhas P ^a   Seddon, Kenneth R ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; NITRIC ACID; ORGANIC SOLVENT; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DIELS ALDER REACTION; HALOGENATION; NITRATION; REACTION ANALYSIS;

EID: 1642271331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036310e     Document Type: Article

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26. 10mim]-[OTf] (2. 5 g) for 18 h to give a monophasic solution (99% conversion by GC analysis). The residual nitric acid and nitrobenzene were separated from the ionic liquid by Kugelrohr distillation from the reaction vessel at 100 °C, 1 mmHg. The nitrobenzene was separated from the dilute nitric acid by phase separation. NMR analysis was in accordance with authentic nitrobenzene (Aldrich). NMR analysis of the ionic liquid showed that it did not undergo nitration in the imidazole ring and was unchanged.
27. Ethyl-3-methylimidazolium hydrogensulfate was synthesized from the reaction of 1-methylimidazole with diethyl sulfate to give 1-ethyl-3- methylimidazolium ethyl sulfate, followed by hydrolysis for 5 days at 100 °C with water. The excess water was distilled off and the ionic liquid dried at 120 °C (1 mmHg) for 48 h.
28. 4), and the isomers of chlorotoluene were purified by Kugelrohr distillation (50-60°C at 10 mmHg). NMR analysis of the ionic liquid showed that it did not undergo chlorination in the imidazole ring and was unchanged.
29. Carmichael, A. J.; Earle, M. J.; Seddon, K. R. World Patent WO 0140146, 2001.
30. 4), and the solvent was evaporated to give 1.15 g of crude product. NMR analysis showed that benzoic acid was the major product (89%), with nitrotoluene isomers as a minor byproduct (2%).