Preparation of 3-methyl-1-(2-(n-propoxy)ethoxycarbonylmethyl)
imidazolium octylsulfate (5f)
19 A. Latala, P. Stepnowski, M. Nedzi and W. Mrozik, Aquat. Tox.,
2
005, 73, 91–98.
0 C. Cho, T. P. Pham, Y. Jeon and Y. Yun, Green Chem., 2008, 10,
7–72.
2
6
To a solution of 3-methyl-1-(2-(n-propoxy)ethoxycarbonyl-
methyl) imidazolium bromide (3.68 g, 12.0 mmol) in distilled
2
2
1 G. Lamberti and K. Kulacki, Green Chem., 2008, 10, 104–110.
2 B. Jastorff, K. Molter, P. Behrend, U. Bottin-Weber, J. Filser, A.
Heimers, B. Ondruschka, J. Ranke, M. Schaefer, H. Schroder, A.
Stark, P. Stepnowski, F. Stock, R. Stormann, S. Stolte, U. Welz-
Biermann, S. Ziegert and J. Thoming, Green Chem., 2005, 7, 362–
water (20 mL) was added in one portion sodium octylsulfate
◦
(
2.09 g, 9.00 mmol). The reaction was stirred at 60 C for 2 h and
then water was slowly removed under vacuum. The precipitate
was dissolved in DCM (10 mL) and washed with distilled water
3
72.
2
2
2
3 P. Balczewski, B. Bachowska, T. Bialas, R. Biczak, W. Wieczorek and
A. Balinska, J. Agric. Food Chem., 2007, 55, 1881–1892.
4 R. P. Swatloski, J. D. Holbrey, S. B. Memon, G. A. Caldwell, K. A.
Caldwell and R. D. Rogers, Chem. Commun., 2004, 668–669.
5 R. J. Bernot, E. E. Kennedy and G. A. Lamberti, Environ. Toxicol.
Chem., 2005, 24, 1759–1765.
(
2 ¥ 5 mL). The product remaining was dried on the rotary
evaporator and then under high vacuum for 8 h to yield a yellow
grease in 85% yield (3.33 g, 7.62 mmol).
1
H NMR (400 MHz, CDCl
3
) d (ppm) 9.45 (s, 1H), 7.48 (t, J =
1
4
6
.6 Hz, 1H), 7.41 (t, J = 1.6 Hz, 1H), 5.25 (s, 2H), 4.36 (t, J =
.7 Hz, 2H), 4.01 (m, 5H), 3.67 (t, J = 4.7 Hz, 2H), 3.43 (t, J =
.8 Hz, 2H), 1.63-1.58 (m, 4H), 1.56-1.29 (m, 10H), 0.92-0.86
26 J. Ranke, A. Muller, U. Bottin-Weber, F. Stock, S. Stolte, J. Arning,
R. Stormann and B. Jastorff, Ecotoxicol. Environ. Safety, 2007, 67,
4
30–438.
2
7 S. Stolte, J. Arnig, U. Bottin-Weber, A. Muller, W. Pitner, U. Welz-
(
m, 6H).
Biermann, B. Jastorff and J. Ranke, Green Chem., 2007, 9, 760–767.
28 A. Garc
´ı a-Lorenzo, E. Tozo, J. Tojo, M. Teijeira, F. J. Rodr ´ı guez-
1
3
C NMR (100 MHz, CDCl
3
) d (ppm) 166.45, 138.89, 123.71,
Berrocal, M. P. Gonz a´ lez and V. S. Mart ´ı nez-Zorzano, Green Chem.,
123.06, 73.04, 67.92, 67.89, 65.67, 49.91, 36.58, 31.83, 29.50,
2
008, 10, 508–516.
2
9.36, 29.26, 25.87, 22.73, 22.66, 14.13, 10.47.
2
3
3
3
3
3
3
3
3
9 F. Stock, J. Hoffmann, J. Ranke, R. Stormann, B. Ondruschka and
B. Jastorff, Green Chem., 2004, 6, 286–290.
0 D. J. Couling, R. J. Bernot, K. M. Docherty, J. K. Dixon and E. J.
Maginn, Green Chem., 2006, 8, 82–90.
1 N. Gathergood and P. J. Scammells, Aust. J. Chem., 2002, 55, 557–
5
-
1
IR (thin film on salt plate) (cm ) 3118, 2958, 2927, 2855, 1750,
569, 1558, 1539, 1495, 1455, 1217, 1178, 1108.
1
-
+
-].
MS m/z, 227.1 [M-OctOSO
3
] ; MS: m/z, 209.0 [OctOSO
3
60.
2 N. Gathergood, M. T. Garcia and P. J. Scammells, Green Chem.,
004, 6, 166–175.
3 M. T. Garcia, N. Gathergood and P. J. Scammells, Green Chem.,
004, 7, 9–14.
Acknowledgements
2
Enterprise Ireland (NG, SM, BP) and the EPA 2006-PHD-
ET-7 studentship (NG, DC) are gratefully acknowledged for
their financial support. We also thank Dr Orla Cahill for her
assistance of DF.
2
4 N. Gathergood, P. J. Scammells and M. T. Garcia, Green Chem.,
2006, 8, 156–160.
5 K. Docherty, J. Dixon and C. Kulpa, Biodegradation, 2007, 18, 481–
4
6 A. Romero, A. Santos, J. Tojo and A. Rodriguez, J. Hazard. Mater.,
2
7 S. Stolte, S. Abdulkarim, J. Arning, A. K. Blomeyer-Nienstedt, U.
Bottin-Weber, M. Matzke, J. Ranke, B. Jastorff and J. Thoming, Green
Chem., 2007, 10, 214–224.
93.
008, 151, 268–273.
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