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The Journal of Organic Chemistry
125.2, 26.6, 26.5, 15.8, 15.7; IR (neat, cm-1): 2914, 1682, 1603, 1356, 1267, 760, 701; HRMS (ESI):
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Calculated for C17H16O (M+Na): 259.1099, found (M+Na): 259.1099.
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1-methoxy-4-(1-phenylprop-1-en-1-yl)benzene 3e);21 Prepared as shown in general procedure. Crude
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reaction mixture was purified on a silica gel column (hexane/EtOAc, 99:1) to obtain the product as
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Colourless oil: Yield: 0.056g (93%), Rf = 0.95 (hexane/EtOAc, 20:1). H NMR (400 MHz, CDCl3): δ
7.36 (t, J = 7.2 Hz, 1H), 7.09-7.3 (m, 7H), 6.79 (d, J = 8.3 Hz, 1H), 6.05-6.014 (m, 1H), 3.83 (s, 1.6H),
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3.83 (s, 1.4H), 1.77 (d, J = 6.9 Hz, 1.5H), 1.73 (d, J = 7.0 Hz, 1.6H); C NMR (100 MHz, CDCl3): δ
158.6, 158.4, 143.4, 141.97, 141.8, 140.3, 135.7, 132.3, 131.2, 128.2, 128.1, 128.0, 127.3, 126.7, 126.6,
123.8, 122.4, 113.4, 55.2, 55.2, 15.8, 15.6; IR (neat, cm-1): 3361, 2925, 1645, 1508, 1245, 702; HRMS
(ESI): Calculated for C16H16O (M+H): 225.1279, found (M+H): 225.1279.
1-methyl-4-(1-phenylprop-1-en-1-yl)benzene (3f); Prepared as shown in general procedure. Crude
reaction mixture was purified on a silica gel column (hexane) to obtain the product as Colorless oil:
Yield: 0.058g (90%) from 4-bromotoluene and 0.043g (90%) from 4-Iodotoluene. Rf = 0.9
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(hexane/EtOAc, 20:1). H NMR (400 MHz, CDCl3): δ 7.36 (t, J = 7.0, 1H), 7.17-7.30 (m, 5H), 7.05-
7.11 (m, 3H), 6.13 (q, J = 7.0 Hz, 1H), 2.38 (s, 1.5H), 2.23 (s, 1.6H), 1.75 (t, J = 8.3 Hz, 3H); 13C NMR
(100 MHz, CDCl3): δ 143.2, 142.22, 142.2, 140.2, 136.9, 136.4, 130.0, 129.9, 128.8, 128.7, 128.0,
127.9, 127.2, 127.0, 126.7, 126.6, 123.9, 123.2, 21.2, 21.0, 15.7, 15.6; IR (neat, cm-1): 3023, 2922,
2855, 1510, 1441, 810, 759, 701.
4-(1-phenylvinyl)phenol (3g); Prepared as shown in general procedure. Crude reaction mixture was
purified on a silica gel column (PE:EA, 20:1) to obtain the product as Colourless oil: Yield: 0.041g
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(72%) from 4-bromophenol. Rf = 0.6 (hexane/EtOAc, 20:1). H NMR (400 MHz, CDCl3): δ 7.306-
7.332 (m, 5H), 7.203-7.245 (m, 4H), 6.7865 (d, J = 8.76 Hz, 2H), 5.38 (d, J = 1.28 Hz, 1H), 5.34 (d, J =
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1.28 Hz, 1H); C NMR (100 MHz, CDCl3): δ 155.4, 149.4, 132.4, 129.6, 128.3, 128.1, 127.6, 117.2,
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