ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
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6.16 (d, 1H, J ¼ 12.5 Hz), 7.02–7.74 (m, 7H), 7.92-7.96 (m, 1H). 13C-NMR (CDCl3): d
45.2, 72.2, 75.3, 121.0–136.5 (10C), 148.2, 151.2, 193.7. MS m/z: 298 (M-H2O), 222, 197,
165, 152, 89, 76, 63, 51.
Anal. Calcd. for C16H13BrO2: C, 60.59; H, 4.13. Found: C, 60.71; H, 4.22.
1-Hydroxy-1-phenyl-octan-3-one (5a)
Colorless oil. IR (neat, cmꢁ1): 3470, 2933, 2885, 1699, 1607, 1451, 1307, 1235, 763,
1
742 cmꢁ1. H-NMR (CDCl3): d 0.80 (t, 3H, J ¼ 7.0 Hz), 1.13-1.27 (m, 5H), 1.46–1.52
(m, 2H), 2.33 (t, 2H, J ¼ 7.5 Hz), 2.67 (dd, 1H, J1 ¼ 3.0 Hz, J2 ¼ 14.0 Hz), 2.77 (dd, 1H,
J1 ¼ 9.0 Hz, J2 ¼ 17.5 Hz), 5.05 (dd, 1H, J1 ¼ 3.0 Hz, J2 ¼ 9.5 Hz), 7.16–7.20 (m, 1H),
7.25–7.26 (m, 4H). 13C-NMR (CDCl3): d 14.0, 22.9, 25.4, 30.8, 42.6, 51.7, 73.7, 126.7,
126.7, 128.2, 128.2, 128.3, 143.8, 209.7. MS m/z: (M) 220, 202, 187, 173, 149, 131, 105,
77, 58.
Anal. Calcd. for C14H20O2: C, 76.33; H, 9.15. Found: C, 76.54; H, 9.25.
1-Hydroxy-1-(4-nitro-phenyl)-octan-3-one (5d)
Pale yellow oil. IR (neat, cmꢁ1): 3338, 2923, 2853, 1615, 1515, 1469, 1384, 1307, 1253,
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1176, 1038, 969, 746 cmꢁ1. H-NMR (CDCl3): d 0.82 (t, 3H, J ¼ 7.0 Hz), 1.15–1.25 (m,
4H), 1.49-1.55 (m, 2H), 2.37 (t, 2H, J ¼ 7.0 Hz), 2.73–2.76 (m, 2H), 3.56 (brs, 1H), 5.19
(dd, 1H, J1 ¼ 4.0 Hz, J2 ¼ 8.5 Hz), 7.46 (d, 2H, J ¼ 8.5 Hz), 8.14 (d, 2H, J ¼ 9.0 Hz). 13C-
NMR (CDCl3): d 14.0, 22.5, 23.4, 31.4, 43.8, 50.4, 69.2, 123.8, 124.0, 126.5, 126.7, 147.5,
150.3, 211.3. MS m/z: (M-1) 254, 247, 208, 195, 153, 141, 127, 113, 101, 87, 77, 63, 51.
Anal. Calcd. for C14H19NO4: C, 63.38; H, 7.22; N, 5.28. Found: C, 63.51; H, 7.36;
N, 5.09.
2-(3-Methyl-benzoyl)-3,4-dihydro-2H-naphthalen-1-one (6b)
Pale orange oil. IR (neat, cmꢁ1): 2985, 2930, 2861, 1726, 1682, 1608, 1528, 1469, 1313,
1208, 1116, 865, 753, 718, 683, 627 cmꢁ1 1H-NMR (CDCl3): d 1.89 (ddd, 1H,
.
J1 ¼ 13.5 Hz, J2 ¼ 8.5 Hz, J3 ¼ 4.5 Hz), 2.49-2.43 (m, 1H), 2.39 (s, 2H), 2.84 (dd, 2H,
J1 ¼ 3.5 Hz, J2 ¼ 1.5 Hz), 4.34 (t, 1H, J ¼ 1.5 Hz), 7.18-7.21 (m, 3H), 7.24–7.31 (m, 2H),
7.37 (dd, 1H, J1 ¼ J2 ¼ 8.5 Hz), 7.52 (ddd, 1H, J1 ¼ 7.5 Hz, J2 ¼ 1.5 Hz, J3 ¼ 15 Hz), 8.13
(dd, 2H, J1 ¼ 8.0 Hz, J2 ¼ 1.5 Hz). 13C-NMR (CDCl3): d 21.3, 25.3, 27.0, 64.2, 123.7,
126.9, 127.2, 128.2, 128.7, 128.8, 129.1, 132.7, 134.0, 134.2, 138.0, 143.3, 193.6, 197.9.
MS m/z: (M) 264, 247, 233, 221, 203, 193, 178, 131, 119, 115, 103, 91, 78.
Anal. Calcd. for C18H16O2: C, 81.79; H, 6.10. Found: C, 81.63; H, 6.27.
2-(4-Nitro-benzoyl)-3,4-dihydro-2H-naphthalen-1-one (6d)
Pale brown oil. IR (neat, cmꢁ1): 2955, 2920, 2854, 1727, 1696, 1601, 1517, 1462, 1347,
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1301, 1232, 1108, 875, 751, 739, 713, 693, 665 cmꢁ1. H-NMR (CDCl3): d 1.69–1.74 (m,
1H), 2.34–2.40 (m, 1H), 2.70-2.86 (m, 2H), 4.40 (t, 1H, J ¼ 1.0 Hz), 7.17 (d, 1H,
J ¼ 10.0 Hz), 7.37 (t, 1H, J ¼ 8.5 Hz), 7.46–7.51 (m, 3H), 8,04 (d, 1H, J ¼ 9.5 Hz), 8.19 (d,