The Journal of Organic Chemistry
Page 18 of 28
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108.1, 60.1, 55.7, 9.1; IR (cm−1) 3010, 2925, 2890, 1439, 1389, 1332, 1260, 1189, 1116, 1028; HRMS
[DART+] m/z: [M + H]+ Calcd for C21H21O2 305.1542, Found 305.1559.
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3’,5’-Dimethoxy-4-methyl-o-terphenyl (2n). 0.42 g, 78% yield. Buff solid; mp 155__158 °C; H NMR
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(400 MHz, CDCl3) δ 7.06__7.17 (m, 5H), 6.93__6.99 (m, 4H), 6.56 (s, 2H), 3.85 (s, 3H), 3.74 (s, 3H), 2.26
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(s, 3H). C NMR (100 MHz, CDCl3) δ 159.4, 158.2, 143.4, 141.9, 135.6, 133.7, 131.5, 129.8, 128.2,
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127.6, 126.3, 122.7, 106.6, 97.9, 55.9, 55.5, 21.3; IR (cm−1) 3020, 2959, 2837, 1584, 1477, 1461, 1343,
1236, 1158, 1107; HRMS [DART+] m/z: [M + H]+ Calcd for C21H21O2 305.1542, Found 305.1529.
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3,5-dimethoxy-2-methy-1,1'-biphenyl (2o). 0.39 g, 70% yield. Pale yellow oil; H NMR (400 MHz,
CDCl3) δ 7.24__7.40 (m, 5H), 6.47 (d, J = 2.4 Hz, 1H), 6.41 (d, J = 2.4 Hz, 1H), 3.82 (s, 3H), 3.78 (s, 3H),
2.03 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 158.6, 158.1, 143.5, 142.1, 129.2, 128.3, 128.1, 126.5, 116.7,
105.6, 97.4, 55.6, 55.4, 12.7; IR (cm−1) 3010, 2995, 2835, 1455, 1412, 1329, 1204, 1143, 1055, 1042;
HRMS [DART+] m/z: [M + H]+ Calcd for C15H17O2 229.1229, Found 229.1230.
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2-Ethyl-3,5-dimethoxy-1,1'-biphenyl (2p). 0.41 g, 74% yield. Pale yellow oil; H NMR (400 MHz,
CDCl3) δ 7.29__7.41 (m, 5H), 6.48 (d, J = 2.4 Hz, 1H), 6.35 (d, J = 2.4 Hz, 1H), 3.84 (s, 3H), 3.78 (s, 3H),
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2.48 (q, J = 7.6 Hz, 2H), 1.01 (t, J = 7.4 Hz, 3H). C NMR (100 MHz, CDCl3) δ 158.6, 157.8, 143.3,
142.2, 129.1, 127.9, 126.8, 123.27, 105.5, 97.7, 55.5, 55.3, 19.9, 14.9; IR (cm−1) 3004, 2958, 2870, 1462,
1414, 1351, 1203, 1144, 1053, 1041; HRMS [DART+] m/z: [M + H]+ Calcd for C16H19O2 243.1385,
Found 243.1370..
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3,5-Dimethoxy-2,4,4’-dimethy-1,1’-biphenyl (2q). 0.43 g, 77% yield. Pale yellow oil; H NMR (400
MHz, CDCl3) δ 7.21 (s diffuse, 4H), 6.55 (s, 1H), 3.78 (s, 3H), 3.73 (s, 3H), 2.39 (s, 3H), 2.20 (s, 3H),
2.13 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 157.6, 156.1, 140.6, 139.3, 136.4, 129.2, 128.8, 120.8, 118.3,
108.1, 59.9, 55.6, 21.2, 13.2, 9.1; IR (cm−1) 3040, 2934, 2863, 1577, 1480, 1445, 1388, 1277, 1232, 1117,
1019; HRMS [DART+] m/z: [M + H]+ Calcd for C17H21O2 257.1542, Found 257.1529.
3,5-dimethoxy-2,4-dimethy-1,1’-biphenyl (2r). 0.38 g, 68% yield. Pale yellow oil; 1H NMR (400 MHz,
CDCl3) δ 7.31__7.43 (m, 5H), 6.56 (s, 1H), 3.81 (s, 3H), 3.75 (s, 3H), 2.21 (s, 3H), 2.12 (s, 3H). 13C NMR
(100 MHz, CDCl3) δ 156.5, 155.1, 141.1, 139.6, 128.2, 126.9, 125.7, 119.6, 117.4, 106.8, 58.8, 54.5, 12.1,
8.05; IR (cm−1) 3002, 2961, 1566, 1463, 1392, 1257, 1114, 1007; HRMS [DART+] m/z: [M + H]+ Calcd
for C16H19O2 243.1385, Found 243.1374.
4’-Methyl-2’,6’-dimethoxy-m-terphenyl (2s). 0.38 g, 71% yield. Pale yellow solid; mp 145__147 °C; 1H
NMR (400 MHz, CDCl3) δ 7.28__7.47 (m, 10H), 6.70 (s, 1H), 3.76 (s, 3H), 2.98 (s, 3H), 2.16 (s, 3H). 13C
NMR (100 MHz, CDCl3) δ 156.4, 156.1, 137.8, 137.3, 134.2, 130.9, 130.8, 130.6, 130.2, 128.8, 128.7,
128.5, 128.1, 127.7, 126.7, 126.6, 122.1, 108.4, 60.3, 55.8, 21.1; IR (cm−1) 3063, 2935, 2848, 1529, 1461,
1388, 1246, 1192, 1097; HRMS [DART+] m/z: [M + H]+ Calcd for C21H21O2 305.1542, Found 305.1558.
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2,4-Dimethoxy-3,6-dimethy-1,1’-biphenyl (2t). 0.42 g, 75% yield. Buff solid; mp 90__93 °C; H NMR
(400 MHz, CDCl3) δ 7.21__7.41 (m, 5H), 6.56 (s, 1H), 3.81 (s, 3H), 3.30 (s, 3H), 2.16 (s, 3H), 2.09 (s,
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