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151.12, 146.76, 136.07, 135.17, 133.29, 129.83, 126.35, 124.18, 3H), 1.27–1.37 (m, 2H), 1.46–1.50 (m, 2H), 4.10 (q, J ¼ 6.0 Hz,
120.38, 75.24.
1H), 5.50 (s, 1H), 6.03 (d, J ¼ 6.0 Hz, 2H); 13C NMR (151 MHz,
2-[(3,4-Dichloro-phenyl)-hydroxy-methyl]-acrylonitrile (Table DMSO-d6) d 133.62, 130.80, 121.05, 73.86, 40.82, 21.30, 17.03.
2, entry 6).4d Yellow oil; 1H NMR (600 MHz, DMSO-d6) d 5.39 (s,
2-(Hydroxy-phenyl-methyl)-acrylic acid methyl ester (Table 2,
1
1H), 6.17 (s, 1H), 6.26 (s, 1H), 6.53 (s, 1H), 7.38 (d, J ¼ 6.0 Hz, entry 17).6c Colorless oil; H NMR (300 MHz, CDCl3) d 3.10 (s,
1H), 7.63 (s, 1H), 7.68 (s, 1H); 13C NMR (151 MHz, DMSO-d6) d 1H), 3.67 (s, 3H), 5.45 (s, 1H), 5.86 (s, 1H), 6.28 (s, 1H), 7.32–7.42
145.60, 134.92, 134.50, 134.18, 133.85, 131.45, 129.89, 129.54, (m, 5H).
120.42, 74.75.
2-[(4-Chloro-phenyl)-hydroxy-methyl]-acrylic acid methyl
2-[(2,4-Dichloro-phenyl)-hydroxy-methyl]-acrylonitrile (Table ester (Table 2, entry 18). White solid; m.p. 44 ꢂC (lit.,6c 43–44 ꢂC);
2, entry 7). White solid; m.p. 73 C (lit.,24 74 C); H NMR (300 1H NMR (300 MHz, CDCl3) d 3.32 (s, 1H), 3.72 (s, 3H), 5.50 (s,
1
ꢂ
ꢂ
MHz, CDCl3) d 3.07 (s, 1H), 5.67 (s, 1H), 6.05 (s, 1H), 7.28 (d, J ¼ 1H), 5.85 (s, 1H), 6.33 (s, 1H), 7.30 (s, 4H).
7.5 Hz, 1H), 7.39 (s, 1H), 7.55 (d, J ¼ 8.01, 1H); 13C NMR (75
2-[Hydroxy-(4-nitro-phenyl)-methyl]-acrylic acid methyl ester
MHz, CDCl3) d 142.57, 137.73, 135.60, 134.09, 131.97, 131.36, (Table 2, entry 19). Yellow solid; m.p. 72 ꢂC (lit.,6c 71–73 ꢂC); 1H
130.38, 126.7, 72.55.
NMR (300 MHz, CDCl3) d 3.23 (s, 1H), 3.42 (s, 3H), 5.45 (s, 1H),
2-[Hydroxy-(4-methoxy-phenyl)-methyl]-acrylonitrile (Table 5.69 (s, 1H), 6.19 (s, 1H), 7.37 (d, J ¼ 6.2 Hz, 2H), 7.98 (d, J ¼ 6.2
2, entry 8).24 Yellow oil; 1H NMR (300 MHz, CDCl3) d 2.25 (s, 1H), Hz, 2H).
3.82 (s, 3H), 5.24 (s, 1H), 6.12 (d, J ¼ 1.3 Hz, 1H), 6.24 (d, J ¼ 1.8
2-(Hydroxy-p-tolyl-methyl)-acrylic acid methyl ester (Table 2,
Hz, 1H), 6.84 (d, J ¼ 7.2 Hz, 2H), 7.32 (d, J ¼ 7.2 Hz, 2H); 13C entry 20). White solid; m.p. 39 ꢂC (lit.,6c 39–42 ꢂC); 1H NMR (400
NMR (75 MHz, CDCl3) d 158.30, 134.72, 129.16, 128.65, 121.48, MHz, CDCl3) d 2.34 (s, 3H), 3.12 (s, 1H), 3.70 (s, 3H), 5.52 (s, 1H),
117.57, 114.86, 74.89, 56.42.
5.83 (s, 1H), 6.29 (s, 1H), 7.15–7.23 (m, 4H).
2-[Hydroxy-(2-methoxy-phenyl)-methyl]-acrylonitrile (Table
2-[(4-Nitro-phenyl)-hydroxy-methyl]-acrylic acid butyl ester
2, entry 9).11a Yellow oil; H NMR (400 MHz, CDCl3) d 3.58 (s, (Table 2, entry 21).6c Pale yellow oil; 1H NMR (400 MHz, CDCl3) d
1H), 3.83 (s, 3H), 5.51 (s, 1H), 5.96 (s, 1H), 5.99 (s, 1H), 6.91 (d, 0.92 (t, J ¼ 7.6 Hz, 3H), 1.39–1.30 (m, 2H), 1.67–1.56 (m, 2H),
J ¼ 8.2 Hz, 1H), 7.01 (t, J ¼ 7.5 Hz, 1H), 7.34 (dd, J ¼ 18.2, 8.4 Hz, 3.42 (br s, 1H), 4.14 (t, J ¼ 6.4 Hz, 2H), 5.63 (s, 1H), 5.87 (s, 1H),
2H); 13C NMR (101 MHz, CDCl3) d 156.45, 129.89, 127.65, 6.41 (s, 1H), 7.60 (d, J ¼ 8.8 Hz, 2H), 8.22 (d, J ¼ 8.4 Hz, 2H).
127.32, 125.90, 121.09, 117.33, 110.96, 70.00, 55.44.
1
2-{[4-(2-Cyano-1-hydroxy-allyl)-phenyl]-hydroxy-methyl}-
Reusability and recovery of the composite system [HyEtPy]Cl–
H2O
acrylonitrile (Table 2, entry 10). White crystal solid; m.p.
134 ꢂC (lit.,17 134.8–135.3 ꢂC); 1H NMR (400 MHz, CDCl3) d 3.78
Aer the rst run of the reaction was completed, the product
was extracted by diethyl ether into the organic layer, and the
remained composite system [HyEtPy]Cl–H2O was directly
reused for the next cycle of the reaction.
(s, 2H), 5.37 (s, 2H), 6.08 (s, 2H), 6.17 (s, 2H), 7.48 (s, 4H); 13C
NMR (101 MHz, DMSO-d6) d 141.17, 130.96, 127.46, 126.76,
117.87, 72.86.
2-[Hydroxy-(4-methyl-phenyl)-methyl]-acrylonitrile (Table 2,
1
entry 11).7c Colorless oil; H NMR (400 MHz, CDCl3) d 2.38 (s,
3H), 3.12 (s, 1H), 5.25 (s, 1H), 6.02 (s, 1H), 6.12 (s, 1H), 7.18–7.23
(m, 4H).
Acknowledgements
We are grateful for nancial support for this work from the Key
Discipline Project of Shanxi Province Education Department
(no. 20141010), the College Students Innovation Project of
Xinzhou Teachers University ([2014]93) and the Key Discipline
Project of Xinzhou Teachers University (no. XK201304).
2-(Hydroxy-naphthalen-1-yl-methyl)-acrylonitrile (Table 2,
1
entry 12).11a Yellow oil; H NMR (600 MHz, DMSO-d6) d 6.04 (s,
1H), 6.20 (s, 1H), 6.36 (s, 1H), 6.46 (s, 1H), 7.56 (dd, J ¼ 19.5, 6.7
Hz, 3H), 7.72 (d, J ¼ 7.1 Hz, 1H), 7.92 (d, J ¼ 8.2 Hz, 1H), 7.97 (d,
J ¼ 9.2 Hz, 1H), 8.19 (d, J ¼ 9.2 Hz, 1H); 13C NMR (151 MHz,
DMSO-d6) d 139.55, 136.79, 134.58, 133.39, 132.07, 131.96,
129.91, 129.56, 129.09, 128.74, 128.08, 127.01, 120.87, 73.31.
2-(Hydroxy-pyridin-2-yl-methyl)-acrylonitrile (Table 2, entry
13).7c Yellow oil; 1H NMR (400 MHz, CDCl3) d 5.29 (s, 1H), 6.08
(s, 1H), 6.25 (s, 1H), 7.32 (d, J ¼ 8.0 Hz, 1H), 7.37 (d, J ¼ 8.0 Hz,
1H), 7.78 (t, J ¼ 6.0 Hz, 1H), 8.60 (d, J ¼ 5.6 Hz, 1H).
Notes and references
1 S. E. Drewes and G. H. P. Roos, Tetrahedron, 1988, 44, 4653.
2 V. K. Aggarwal and A. Mereu, Chem. Commun., 1999, 2311.
3 (a) F. Ameer, S. E. Drewes, S. Freese and P. T. Kaye, Synth.
Commun., 1988, 18, 495; (b) V. K. Aggarwal, I. Emme and
S. Y. Fulford, J. Org. Chem., 2003, 68, 692.
4 (a) D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron,
1996, 52, 8001; (b) D. Basavaiah, J. Rao and
T. Satyanarayana, Chem. Rev., 2003, 103, 811; (c) F.-L. He,
Y. Wei and M. Shi, Chem. Commun., 2014, 50, 8912; (d)
R. O. M. A. de Souza, B. A. Meireles, L. C. S. Aguiar and
M. L. A. A. Vasconcellos, Synthesis, 2004, 1596.
2-(Furan-2-yl-hydroxy-methyl)-acrylonitrile (Table 2, entry
14).7c Colorless oil; 1H NMR (400 MHz, CDCl3) d 2.48 (br s, 1H),
5.39 (s, 1H), 6.08 (s, 1H), 6.18 (d, J ¼ 4.0 Hz, 1H), 6.29 (d, J ¼ 4.0
Hz, 1H), 6.44 (d, J ¼ 3.9 Hz, 1H), 7.36 (d, J ¼ 4.0 Hz, 1H).
3-Hydroxy-2-methylene-butyronitrile (Table 2, entry 15).9a
Yellow oil; 1H NMR (300 MHz, CDCl3) d 3.32 (s, 1H), 3.71 (s, 3H),
5.50 (s, 1H), 5.85 (s, 1H), 6.33 (s, 1H); 13C NMR (75 MHz, CDCl3)
d 128.7, 119.7, 117.3, 68.1, 19.6.
3-Hydroxy-2-methylene-hexanenitrile (Table 2, entry 16).9a
5 (a) D. Basavaiah, B. S. Reddy and S. S. Badsara, Chem. Rev.,
2010, 110, 5447; (b) D. K. Nair, R. F. S. Menna-Barreto,
1
Yellow oil; H NMR (600 MHz, DMSO-d6) d 0.88 (d, J ¼ 6.0 Hz,
32844 | RSC Adv., 2015, 5, 32839–32845
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