Study of the Application of Functional Ionic Liquid
J. Chin. Chem. Soc., Vol. 55, No. 5, 2008 1127
3023, 2924, 1688, 1625, 1572, 1485, 771, 694 cm-1. H
1
Scheme II
NMR (CDCl3, 400 MHz) d: 7.81 (s, 2H, CH=), 7.49-7.34
(m, 10H, Ar-H), 2.97-2.94 (t, 4H, J = 3.2 Hz, CH2CH2CH2),
1.83-1.80 (m, 2H, CH2CH2CH2).
3f: yellow solid, M.p. 146.7-147.9 °C. IR (KBr) u:
3058, 2965, 1659, 1606, 1566, 1487, 830 cm-1. 1H NMR
(CDCl3, 400 MHz) d: 7.74 (s, 2H, CH=), 7.40-7.37 (m, 8H,
Ar-H), 2.92-2.89 (m, 4H, CH2CH2CH2), 1.85-1.79 (m, 2H,
CH2CH2CH2).
3g: yellow solid, M.p. 182.7-184.3 °C. IR (KBr) u:
1
3502, 2909, 1688, 1607, 1549, 783, 668 cm-1. H NMR
(CDCl3, 400 MHz) d: 7.74 (s, 2H, CH=), 7.52 (m, 6H, Ar-
H), 7.35-7.31 (m, 2H, Ar-H), 3.13 (s, 4H, CH2CH2).
3k: brown solid, M.p. 140.8-142.5 °C. IR (KBr) u:
1
3148, 2947, 1635, 1583, 1540, 744 cm-1. H NMR (300
MHz, CDCl3) d: 7.56-7.55 (m, 4H, fural-H), 6.68 (brs, 1H,
CH=), 6.67 (brs, 1H, CH=), 6.53-6.51 (m, 2H, fural-H),
3.03-3.99 (m, 4H, CH2CH2CH2), 1.90-1.87 (m, 2H,
CH2CH2CH2). MS (ESI): 255 (M+1)+, 309 (M+CH3OH+
Na).
ACKNOWLEDGEMENT
WRS-IB digital melting point instrument. IR spectra were
measured on a Nicolet NEXUS 470 FT-IR Infrared spec-
trophotometer in KBr pellets. 1H NMR were recorded on
Bruker AM-400 spectrometer or Bruker AM-300 spec-
trometer with TMS as an internal standard. Mass spectra
were recorded on a Teheran 8430 mass spectrometer.
General procedure for the synthesis of 3a-i
This work was financially supported by Science and
Technology Foundation of Shanghai Institute of Technol-
ogy (No. QT2006-07).
Received August 9 2007.
REFERENCES
Cycloalkanone (1 mmol), aromatic aldehyde (2
mmol), and amino-functionalized ionic liquids11 (1 mL)
were added in a Pyrex beaker (50 mL). The mixture was
stirred at 80 °C for a certain period of time to complete the
reaction (monitored by TLC). After cooling, the product
was extracted with chloroform (3 ´ 20 mL). The organic
was washed with water, dried with anhydrous magnesium
sulfate and evaporated. Recrystallization of the product
with ethanol or purification after column chromatography
afforded the crystalline products (80-92%). The solution
containing the ionic liquid was then recovered for reuse by
drying at 60 °C under decompress for several hours. The
condensation of different substituted benzaldehydes and
cyclopentanone or cyclohexanone was carried out in the
presence of amino-functionalized ionic liquid. The results
are summarized in Table 2.
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Selected characterization data
3b: yellow solid, M.p. 116.1-116.6 °C. IR (KBr) u: