Convenient Synthesis of 1-Arylmethyl-2-naphthols
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1-(4-Methylbenzyl)-2-naphthol (11). H NMR (300 MHz, CDCl3) d: 2.32
(3H, s, Ar-CH3), 4.45 (2H, s, Ar-CH2-Ar0), 7.08–7.16 (4H, m, Ar-H),
7.34–7.48 (3H, m, Ar-H), 7.70–7.98 (3H, m, Ar-H). 13C NMR (75 MHz,
CDCl3) d: 21.43, 30.70, 118.36, 118.75, 123.62, 123.76, 126.78, 126.93,
127.08, 128.50, 128.87, 128.96, 129.74, 129.87, 134.08, and 151.66. IR,
KBr disc, v: 3435, 3026, 3017, 2972, 1615, 1600, 1468, 709 cm21. EI-MS
(70 eV) m/z (% int.): 248 (Mþ, 100), 156 (4), 144 (5), 105 (5). HR-MS
calcd. for C18H16O: 248.1201; found: 248.1195.
1-(4-Aminobenzyl)-2-naphthol (12). 1H NMR (300 MHz, DMSO-d6) d: 3.58
(2H, bs, NH2), 4.16 (2H, s, Ar-CH2-Ar0), 6.40 (2H, m, Ar0-H), 6.87 (2H, m,
Ar0-H), 7.21–7.39 (3H, m, Ar-H), 7.64–7.85 (3H, m, Ar-H), 9.63
(1H, bs, OH). 13C NMR (75 MHz, DMSO-d6) d: 29.89, 49.46, 114.70,
119.01, 119.73, 123.00, 124.09, 126.79, 128.24, 129.10, 129.19, 129.42,
134.18, 147.07, and 153.17. IR, KBr disc, v: 3420, 3359, 3298, 1631, 1613,
1512, 1384, 807, 745 cm21. EI-MS (70 eV) m/z (% int.): 249 (Mþ, 7), 144
(100), 115 (5), 93 (7). HR-MS calcd. for C17H15NO: 249.1154; found:
249.1148.
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1-(4-Methoxybenzyl)-2-naphthol (13). H NMR (300 MHz, DMSO-d6) d:
3.65 (3H, s, O-CH3), 4.29 (2H, s, Ar-CH2-Ar0), 6.77 (2H, d, J ¼ 8.2 Hz,
Ar0-H), 7.08–7.41 (5H, m, Ar-H), 7.65–7.87 (3H, m, Ar-H), 9.72 (1H, bs,
OH). 13C NMR (75 MHz, DMSO-d6) d: 29.82, 55.76, 114.43, 118.99,
119.19, 123.08, 123.90, 126.96, 128.53, 128.95, 129.11, 129.15, 129.90,
134.08, 153.28, and 157.04. IR, KBr disc, v: 3367, 2926, 1630, 1607, 1584,
1510, 1384, 808, 745 cm21. EI-MS (70 eV) m/z (% int.): 264 (Mþ, 100),
108 (54). HR-MS calcd. for C18H16O2: 264.1150; found: 264.1152.
1-((Pyridine-4-yl)methyl)-2-naphthol (14). 1H NMR (300 MHz, DMSO-d6)
d: 4.36 (2H, s, Ar-CH2-Ar0), 7.18–7.39 (5H, m, Ar-H), 7.72–7.81 (3H, m, Ar-
H), 8.37–8.38 (2H, m, Ar-H), 10.10 (1H, bs, OH). 13C NMR (75 MHz,
DMSO-d6) d: 30.19, 117.02, 118.92, 123.28, 123.53, 124.56, 127.30,
129.06, 129.16, 129.29, 133.99, 150.17, 151.34, and 153.70. IR, KBr disc,
v: 3448, 3051, 2967, 2937, 1607, 1576, 1438, 1332, 1277, 808, 519 cm21
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EI-MS (70 eV) m/z (% int.): 235 (Mþ, 100), 157 (2). HR-MS calcd. for
C16H13NO: 235.0997; found: 235.0993.
1-((Pyridine-2-yl)methyl)-2-naphthol (15). Prepared by methods A and B.
1H NMR (300 MHz, DMSO-d6) d: 4.49 (2H, s, CH2), 7.02–7.45 (5H, m,
Ar-H), 7.53–8.00 (4H, m, Ar-H), 8.48 (1H, d, J ¼ 8.2 Hz, Ar0-H), 9.98
(1H, bs, OH). 13C NMR (75 MHz, DMSO-d6) d: 34.14, 117.71, 119.17,
122.07, 123.16, 123.21, 123.97, 127.09, 128.23, 128.91, 129.10, 134.26,
137.55, 149.47, 153.59, and 161.88. IR, KBr disc, v: 3444, 3058, 2953,
2923, 1631, 1618, 1596, 1384, 750 cm21. EI-MS (70 eV) m/z (% int.): 235