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119.24, 116.88, 70.03 ppm. Anal. calcd for C13H10N2O: C, 74.27;
H, 4.79; N, 13.33; found: C, 74.31; H, 4.77; N, 13.38.
2-(Hydroxy-phenyl-methyl)-acrylic acid methyl ester (Table 2,
entry 20)14b
1
Colorless oil; H NMR (400 MHz, CDCl3) d 7.32–7.42 (m, 5H),
6.28 (s, 1H), 5.86 (s, 1H), 5.45 (s, 1H), 3.67 (s, 3H), 3.10 (s, 1H)
ppm.
2-[Hydroxy-(4-hydroxy-3-methoxy-phenyl)-methyl]-
acrylonitrile (Table 2, entry 14)19a
Pale yellow solid, mp 110.6 ꢀC; 1H NMR (400 MHz, CDCl3) d 7.32
(s, 1H), 7.29 (s, 1H), 7.18 (s, 1H), 5.08 (s, 2H), 4.16 (s, 1H), 3.97 (s,
3H) ppm; 13C NMR (101 MHz, CDCl3) d 148.35, 141.74, 134.90,
129.35, 124.42, 122.20, 119.15, 118.05, 74.72, 55.96. Anal. calcd
for C11H11NO3: C, 64.38; H, 5.40; N, 6.83; found: C, 64.34; H,
5.42; N, 6.79.
2-[(4-Chloro-phenyl)-hydroxy-methyl]-acrylic acid methyl ester
(Table 2, entry 21)
1
White solid; mp 44.1 C (lit.,14b 43–44 C); H NMR (400 MHz,
CDCl3) d 7.30 (s, 4H), 6.33 (s, 1H), 5.86 (s, 1H), 5.50 (s, 1H), 3.72
(s, 3H), 3.32 (s, 1H) ppm.
ꢀ
ꢀ
2-[Hydroxy-(4-nitro-phenyl)-methyl]-acrylic acid methyl ester
(Table 2, entry 22)
2-[Hydroxy-(4-chloro-3-nitro-phenyl)-methyl]-acrylonitrile
(Table 2, entry 15)14d
1
Yellow solid, mp 72.3 C (lit.,14b 71–73 C); H NMR (400 MHz,
ꢀ
ꢀ
CDCl3) d 8.19 (d, J ¼ 8.8 Hz, 2H), 7.57 (d, J ¼ 8.7 Hz, 2H), 6.40 (s,
Yellow oil; 1H NMR (400 MHz, CDCl3) d 7.76 (s, 2H), 7.39 (s, 2H),
6.04 (s, 1H), 5.90 (s, 1H), 5.21 (s, 1H), 3.00 (s, 1H) ppm; 13C NMR
(101 MHz, CDCl3) d 150.99, 142.85, 134.72, 133.93, 130.58,
129.07, 127.92, 126.00, 116.85, 74.18 ppm.
1H), 5.90 (s, 1H), 5.63 (s, 1H), 3.74 (s, 3H), 3.51 (s, 1H) ppm; 13
C
NMR (101 MHz, CDCl3) d 166.39, 148.69, 147.40, 140.98, 127.39,
127.26, 123.62, 72.60, 52.24 ppm.
2-[(4-Chloro-3-nitro-phenyl)-hydroxy-methyl]-acrylic acid
methyl ester (Table 2, entry 23)
2-[(3,4-Dichloro-phenyl)-hydroxy-methyl]-acrylonitrile (Table
2, entry 16)25
White solid, mp 85.4 ꢀC (lit.,14d 84 ꢀC); 1H NMR (400 MHz,
CDCl3) d 7.92 (s, 1H), 7.55 (q, J ¼ 8.4 Hz, 2H), 6.42 (s, 1H), 5.94 (s,
1H), 5.59 (s, 1H), 3.76 (s, 3H), 3.45 (s, 1H) ppm; 13C NMR (101
MHz, CDCl3) d 166.25, 147.87, 142.17, 140.70, 131.76, 131.16,
127.36, 126.11, 123.61, 72.05, 52.25 ppm.
1
Yellow oil; H NMR (600 MHz, DMSO-d6) d 7.67 (d, J ¼ 8.3 Hz,
1H), 7.63 (d, J ¼ 2.0 Hz, 1H), 7.38 (dd, J ¼ 8.6, 2.3 Hz, 1H), 6.53
(s, 1H), 6.26 (d, J ¼ 1.0 Hz, 1H), 6.17 (s, 1H), 5.39 (d, J ¼ 4.2 Hz,
1H) ppm; 13C NMR (151 MHz, DMSO-d6) d 145.60, 134.92,
134.47, 134.07, 133.85, 131.52, 129.89, 129.54, 120.42, 74.75
ppm.
2-[Hydroxy-(3-hydroxy-phenyl)-methyl]-acrylic acid methyl
ester (Table 2, entry 24)19a
Pale yellow solid, mp 100.4 ꢀC; 1H NMR (400 MHz, CDCl3) d 7.22
(t, J ¼ 7.8 Hz, 1H), 6.91 (d, J ¼ 12.3 Hz, 2H), 6.78 (s, 1H), 6.36 (s,
1H), 5.86 (s, 1H), 5.66 (s, 1H), 5.53 (s, 1H), 3.75 (s, 3H), 3.27 (s,
1H) ppm; 13C NMR (101 MHz, CDCl3) d 166.87, 155.81, 143.16,
141.73, 129.75, 126.54, 118.87, 114.87, 113.45, 73.13, 51.89 ppm.
Anal. calcd for C11H12O4: C, 63.45; H, 5.81; found: C, 63.34; H,
5.75.
2-[(2,4-Dichloro-phenyl)-hydroxy-methyl]-acrylonitrile (Table
2, entry 17)
White solid, mp 73.5 ꢀC (lit.,14d 74 ꢀC); 1H NMR (400 MHz,
CDCl3) d 7.55 (d, J ¼ 8.01, 1H), 7.38 (s, 1H), 7.31 (d, J ¼ 8.01 Hz,
1H), 6.08 (s, 1H), 5.69 (s, 1H), 3.12 (s, 1H) ppm; 13C NMR (101
MHz, CDCl3) d 141.67, 137.14, 136.07, 134.81, 130.29, 129.22,
128.12, 125.76, 118.42, 72.20 ppm.
2-(Hydroxy-quinolin-4-yl-methyl)-acrylic acid ethyl ester (Table
2, entry 25)
1
ꢀ
2-{[4-(2-Cyano-1-hydroxy-allyl)-phenyl]-hydroxy-methyl}-
acrylonitrile (Table 2, entry 18)
White crystal solid, mp 134.2 ꢀC (lit.,19d 134.8–135.3 ꢀC); 1H
NMR (400 MHz, CDCl3) d 7.48 (s, 5H), 6.17 (s, 2H), 6.08 (s, 2H),
5.37 (s, 2H), 3.77 (s, 2H) ppm; 13C NMR (101 MHz, DMSO-d6)
d 141.17, 130.96, 127.46, 126.76, 117.87, 72.86 ppm.
White solid, mp 87.4 C; H NMR (400 MHz, CDCl3) d 8.80 (s,
1H), 8.06 (s, 1H), 7.97 (s, 1H), 7.67–7.51 (m, 2H), 6.38 (s, 2H),
5.64 (s, 1H), 4.21 (s, 1H), 2.60 (s, 1H), 1.24–1.12 (m, 3H) ppm; 13
C
NMR (101 MHz, CDCl3) d 166.34, 150.11, 147.98, 147.40, 141.81,
129.82, 129.19, 127.28, 126.68, 125.93, 123.83, 118.98, 67.74,
61.22, 14.06 ppm. Anal. calcd for C15H15NO3: C, 70.02; H, 5.88;
N, 5.44; found: C, 70.26; H, 5.91; N, 5.48 ppm.
3-Hydroxy-2-methylene-hexanenitrile (Table 2, entry 19)19a
2-(Hydroxy-quinolin-4-yl-methyl)-acrylic acid butyl ester
(Table 2, entry 26)
1
Yellow oil; H NMR (600 MHz, DMSO-d6) d 6.03 (d, J ¼ 6.3 Hz,
2H), 5.50 (s, 1H), 4.10 (s, 1H), 1.48 (dd, J ¼ 15.1, 7.4 Hz, 2H), White solid, mp 104.2 ꢀC; 1H NMR (400 MHz, CDCl3) d 8.88 (d, J
1.35–1.25 (m, 2H), 0.87 (d, J ¼ 7.4 Hz, 3H) ppm; 13C NMR (151 ¼ 4.5 Hz, 1H), 8.12 (d, J ¼ 8.4 Hz, 1H), 7.96 (d, J ¼ 8.4 Hz, 1H),
MHz, DMSO-d6) d 133.62, 130.80, 121.05, 73.86, 43.37, 43.23, 7.70 (t, J ¼ 7.7 Hz, 1H), 7.61 (d, J ¼ 4.5 Hz, 1H), 7.54 (t, J ¼ 7.6 Hz,
43.09, 42.95, 42.82, 42.68, 42.54, 40.82, 21.30, 17.03 ppm.
1H), 6.39 (s, 2H), 5.57 (s, 1H), 4.20 (t, J ¼ 5.1 Hz, 2H), 1.66–1.59
This journal is © The Royal Society of Chemistry 2016
RSC Adv., 2016, 6, 62778–62784 | 62783