(s, 1 H), 2.05 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 2 H), 1.02 (t, J =
7.5 Hz, 3 H); 13C-NMR (CDCl3, 75 MHz, ppm): d = 153.1, 140.5,
135.2, 135.1, 130.8, 129.3, 128.7, 127.7, 126.6, 125.8, 120.7, 115.5,
23.5, 14.2; IR (KBr, cm-1): v = 3524, 2966, 2872, 1580, 1486, 1449,
1334, 1284, 1193, 1148, 1033, 910, 828, 755, 698; HRMS calc.
C16H16O (M+): 224.1201. Found: 224.1204.
J2 = 7.5 Hz, 2 H), 1.99 (s, 3 H), 1.07 (t, J = 7.5 Hz, 3 H); 13C-
NMR (CDCl3, 75 MHz, ppm): d = 152.0, 133.5, 131.6, 131.1,
128.4, 128.2, 120.3, 115.4, 21.9, 17.9, 14.2; IR (KBr, cm-1): v =
3512, 2965, 2873, 1578, 1487, 1448, 1340, 1282, 1222, 1182, 1037,
909, 828, 753; GC-MS (EI) calc. C11H14O (M+): 162. Found: 162.
(E)-4-Methoxy-2-(pent-2-en-2-yl)phenol (2k). The title com-
pound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm): d =
6.86–6.82 (m, 1 H), 6.75–6.71 (m, 1 H), 6.58 (d, J = 7.5 Hz, 1 H),
5.69 (t, J = 7.5 Hz, 1 H), 4.83 (s, 1 H), 3.76 (s, 3 H), 1.97 (s, 3 H),
1.85 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 2 H), 0.92 (t, J = 7.5 Hz, 3 H);
13C-NMR (CDCl3, 75 MHz, ppm): d = 145.7, 133.4, 130.8, 115.5,
113.9, 113.8, 113.2, 112.4, 55.9, 25.1, 22.7, 14.2; IR (KBr, cm-1):
v = 3450, 2962, 2873, 1589, 1493, 1423, 1364, 1275, 1218, 1165,
1040, 856, 810, 762; GC-MS (EI) calc. C12H16O2 (M+): 192. Found:
192.
Deuterium (E)-2-(1-phenylbut-1-enyl)phenol (2a-d). The title
compound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm):
d = 7.28–7.23 (m, 6 H), 7.02–6.94 (m, 3 H), 6.37 (t, J = 7.5 Hz,
1 H), 5.02 (s, 1 H), 2.05 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 1 H),
1.03 (t, J = 7.5 Hz, 3 H); 13C-NMR (CDCl3, 75 MHz, ppm): d =
153.1, 140.5, 135.2, 135.1, 130.8, 129.3, 128.7, 127.7, 126.6, 125.8,
120.7, 115.5, 23.5, 14.2; IR (KBr, cm-1): v = 3524, 2966, 2872,
1580, 1486, 1449, 1334, 1284, 1193, 1148, 1033, 910, 838, 755, 698;
HRMS calc. C16H15DO (M+): 225.1264. Found: 225.1258.
(E)-4-Methoxy-2-(1-phenylbut-1-enyl)phenol (2f). The title
compound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm):
d = 7.35–7.12 (m, 5 H), 6.91–6.80 (m, 2 H), 6.56 (s, 1 H), 6.36 (t,
J = 7.5 Hz, 1 H), 4.73 (s, 1 H), 3.72 (s, 3 H), 2.06 (dq, J1 = 7.5 Hz,
J2 = 7.5 Hz, 2 H), 1.03 (t, J = 7.5 Hz, 3 H); 13C-NMR (CDCl3,
75 MHz, ppm): d = 153.7, 147.2, 135.8, 134.9, 129.2, 128.6, 127.6,
126.5, 116.5, 116.0, 115.7, 115.4, 55.8, 23.4, 14.0; IR (KBr, cm-1):
v = 3528, 2964, 2872, 1596, 1491, 1446, 1360, 1274, 1212, 1145,
1039, 952, 852, 772, 697; HRMS calc. C17H18O2 (M+): 254.1307.
Found: 254.1302.
(E)-4-Bromo-2-(pent-2-en-2-yl)phenol compound with (Z)-4-
bromo-2-(pent-2-en-2-yl)phenol (17:20) (2l). The title mixture
was a yellow oil (with a trace of byproducts from NMR). 1H-NMR
(CDCl3, 300 MHz, ppm): d = 7.27–7.14 (m, 2 H), 6.82–6.77 (m,
1 H), 5.22 (m, 0.38 H), 5.63 (s, 0.5 H), 5.55 (m, 0.51 H), 5.26 (s,
0.5 H), 2.28–2.18 (m, 1.11 H), 1.96 (s, 3 H), 1.88–1.80 (m, 0.95
H), 1.06 (t, J = 7.5 Hz, 1.64 H), 0.93 (t, J = 7.5 Hz, 1.19 H);
13C-NMR (CDCl3, 75 MHz, ppm): d = 151.5, 134.1, 134.0, 131.0,
130.8, 130.6, 117.0, 116.6, 24.7, 22.4, 21.6, 20.9, 14.0, 13.8; IR
(KBr, cm-1): v = 3511, 2965, 2874, 1594, 1481, 1403, 1376, 1265,
1210, 1175, 1044, 909, 816, 759, 734; GC-MS(EI): two peaks and
both are 240.
(E)-4-Chloro-2-(1-phenylbut-1-enyl)phenol (2g). The title com-
pound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm): d =
7.30–7.21 (m, 6 H), 7.04–6.92 (m, 2 H), 6.40 (t, J = 7.5 Hz, 1 H),
5.07 (s, 1 H), 2.07 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 2 H), 1.06 (t,
J = 7.5 Hz, 3 H); 13C-NMR (CDCl3, 75 MHz, ppm): d = 152.2,
135.7, 133.4, 130.1, 129.1, 128.7, 127.8, 126.5, 116.7, 23.4, 13.9; IR
(KBr, cm-1): v = 3522, 2966, 2872, 1597, 1480, 1408, 1326, 1266,
1194, 1079, 943, 881, 764, 666; HRMS calc. C16H15ClO (M+):
258.0811. Found: 258.0816.
(E)-2,4-Di-tert-butyl-6-(pent-2-en-2-yl)phenol (2m). The title
compound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm):
d = 7.19 (d, J = 2.7 Hz, 1 H), 6.93 (d, J = 2.7 Hz, 1 H), 5.80 (s, 1 H),
5.05 (t, J = 7.5 Hz, 1 H), 2.23 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 2 H),
2.00 (s, 3 H), 1.07 (t, J = 7.5 Hz, 3 H); 13C-NMR (CDCl3, 75 MHz,
ppm): d = 148.1, 141.5, 135.0, 133.8, 133.5, 132.4, 122.6, 115.4,
35.3, 34.4, 31.8, 29.8, 21.9, 18.5, 14.2; IR (KBr, cm-1): v = 3506,
2961, 2872, 1600, 1489, 1442, 1362, 1264, 1201, 1168, 1119, 1032,
909, 878, 817, 767, 648; HRMS calc. C19H30O (M+): 274.2297.
Found: 274.2295.
(E)-2-(1-p-Tolylbut-1-enyl)phenol (2h). The title compound
1
was a yellow oil. H-NMR (CDCl3, 300 MHz, ppm): d = 7.24–
6.92 (m, 8 H), 6.34 (t, J = 7.5 Hz, 1 H), 5.04 (s, 1 H), 2.31 (s, 3 H),
2.04 (dq, J1 = 7.5 Hz, J2 = 7.5 Hz, 2 H), 1.01 (t, J = 7.5 Hz, 3 H);
13C-NMR (CDCl3, 75 MHz, ppm): d = 153.5, 138.2, 135.3, 134.0,
130.6, 130.4, 129.3, 129.1, 128.8, 126.4, 120.5, 120.3, 115.3, 23.3,
21.1, 14.0; IR (KBr, cm-1): v = 3515, 2965, 2872, 1606, 1484, 1457,
1334, 1284, 1196, 1035, 932, 817, 754, 685; HRMS calc. C17H18O
(M+): 238.1358. Found: 238.1353.
(E)-2-(But-1-enyl)phenol (2n). The title compound was a yel-
1
low oil. H-NMR (CDCl3, 300 MHz, ppm): d = 7.30 (d, J =
7.5 Hz, 1 H), 7.10–7.05 (m, 1 H), 6.89–6.84 (m, 1 H), 6.77 (d, J =
8.1 Hz, 1 H), 6.55 (d, J = 15.9 Hz, 1 H), 6.28–6.19 (m, 1 H), 5.10
(s, 1 H), 2.27–2.22 (m, 2 H), 1.09 (t, J = 7.5 Hz, 3 H); 13C-NMR
(CDCl3, 75 MHz, ppm): d = 153.0, 135.3, 128.1, 127.9, 127.5,
123.2, 121.0, 115.8, 26.6, 13.8; IR (KBr, cm-1): v = 3424, 2964,
2872, 1605, 1486, 1455, 1331, 1242, 1132, 1087, 971, 908, 879, 798,
750; GC-MS (EI) calc. C10H12O (M+): 148. Found: 148.
(E)-4-Bromo-2-(1-p-tolylbut-1-enyl)phenol (2i). The title com-
pound was a yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm): d =
7.37–7.33 (m, 1 H), 7.16–7.08 (m, 5 H), 6.87 (d, J = 5.7 Hz, 1 H),
6.34 (t, J = 7.5 Hz 1 H), 5.01 (s, 1 H), 2.33 (s, 3 H), 2.04 (dq, J1 =
7.5 Hz, J2 = 7.5 Hz, 2 H), 1.03 (t, J = 7.5 Hz, 3 H); 13C-NMR
(CDCl3, 75 MHz, ppm): d = 152.9, 138.1, 137.9, 134.9, 133.0,
132.0, 129.6, 129.5, 129.2, 126.5, 117.3, 112.3, 23.4, 21.2, 14.1; IR
(KBr, cm-1): v = 3516, 2965, 2871, 1569, 1476, 1412, 1325, 1264,
1195, 1074, 941, 817, 720, 611; HRMS calc. C17H17BrO (M+):
316.0463. Found: 316.0469.
(E)-4-Bromo-2-(but-1-enyl)phenol (2o). The title compound
1
was a yellow oil. H-NMR (CDCl3, 300 MHz, ppm): d = 8.13
(s,1 H), 7.27–7.24 (m, 1 H), 7.04–7.03 (m, 1 H), 6.74 (d, J =
8.4 Hz, 1 H), 5.82–5.64 (m, 1 H), 5.09 (s, 1 H), 3.58–3.51 (m, 2 H),
1.24 (t, J = 6.9 Hz, 3 H); 13C-NMR (CDCl3, 75 MHz, ppm): d =
155.1, 133.7, 131.8, 130.8, 130.3, 118.9, 118.0, 111.7, 40.5, 13.9; IR
(KBr, cm-1): v = 3339, 2976, 2876, 1578, 1481, 1370, 1246, 1167,
1075, 993, 912, 819, 734; HRMS calc. C10H11BrO (M+): 225.9993.
Found: 225.9988.
(E)-2-(Pent-2-en-2-yl)phenol (2j). The title compound was a
yellow oil. 1H-NMR (CDCl3, 300 MHz, ppm): d = 7.18–7.07 (m,
2 H), 6.93–6.88 (m, 2 H), 5.64–5.52 (m, 2 H), 2.24 (dq, J1 = 7.5 Hz,
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The Royal Society of Chemistry 2009
Org. Biomol. Chem., 2009, 7, 3168–3172 | 3171
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