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FUNCTIONALIZED BENZOPHENONES
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129.4, 125.8, 112.7, 110.3, 56.6, 56.6, 22.2. Found: C, 73.48; H, 6.44%.
C16H16O3ꢁ0.25H2O requires: C, 73.69; H, 6.38%.
Using this method there was also obtained:
2,3,4-Dimethoxy-40-methylbenzophenone (Run 2): pale yellow oil after
chromatography (SiO2, PE/EtOAc, 2 : 1), crystallising on standing, m.p.
77–80ꢀC. H NMR (CDCl3) ꢀ 7.72 (d, 2H, o-Ph), 7.24 (d, 2H, m-Ph), 7.12
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(d, 1H, J ¼ 8.5 Hz, H-6), 6.73 (d, 1H, J ¼ 8.5 Hz, H-5), 3.95 (s, 3H, OCH3),
3.93 (s, 3H, OCH3), 3.77 (s, 3H, OCH3), 2.43 (s, 3H, CH3). 13C NMR
(CDCl3) ꢀ 195.8, 156.5, 153.1, 144.2, 142.6, 136.3, 130.6, 129.8, 127.3, 125.5,
107.3, 62.4, 61.6, 56.7, 22.3. Found: C, 71.09; H, 6.68%. C17H18O4 requires:
C, 71.31; H, 6.33%.
3,4-Dimethoxy-30,40-dichlorobenzophenone (Run 3): white crystals
(CH2Cl2/PE), m.p. 99–101ꢀC. H NMR (CDCl3) ꢀ 7.87 (d, 1H, J ¼ 1.9 Hz,
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H-20), 7.60 (dd, 1H, J ¼ 1.9 and 8.4 Hz, H-60), 7.59 (d, 1H, J ¼ 8.4 Hz, H-50),
7.47 (d, 1H, J ¼ 2.1 Hz, H-2), 7.34 (dd, 1H, J ¼ 2.1 and 8.4 Hz, H-6), 6.92
(d, 1H, J ¼ 8.4 Hz, H-5), 3.99 (s, 3H, OCH3), 3.96 (s, 3H, OCH3). 13C NMR
(CDCl3) ꢀ 193.6, 154.1, 149.8, 138.5, 137.0, 133.4, 132.1, 130.9, 129.9, 129.4,
126.0, 112.4, 110.4, 56.7, 56.7. Found: C, 57.78; H, 4.12%. C17H18O4
requires: C, 57.90; H, 3.89%.
3,4-Dimethoxy-30,40-dimethoxybenzophenone (Run 4): white crystals
(EtOH), m.p. 148–150ꢀC. 1H NMR (CDCl3) ꢀ 7.45 (d, 2H, J ¼ 1.9 Hz,
H-2, H-20), 7.39 (dd, 2H, J ¼ 1.9 and 8.2 Hz, H-6, H-60), 6.92 (d, 2H,
J ¼ 8.2 Hz, H-5, H-50), 3.98 (s, 6H, 2 ꢂ OCH3), 3.95 (s, 6H, 2 ꢂ OCH3).
13C NMR (CDCl3) ꢀ 195.1, 153.1, 149.4, 131.3, 125.3, 112.8, 110.3, 56.6,
56.6. Found: C, 67.65; H, 5.59%. C17H18O4 requires: C, 67.54; H, 6.00%.
3,4-Dimethoxy-naphthalenone (Run 5): greyish crystals (EtOH), m.p.
122–123ꢀC. 1H NMR (CDCl3) ꢀ 8.26 (s, 1H, H-10), 8.0–7.85 (m, 4H, Ar–H),
7.65–7.5 (m, 3H, Ar–H, H-2), 7.47 (dd, 1H, J ¼ 2.1 and 8.4 Hz, H-6), 6.94
(d, 1H, J ¼ 8.4 Hz, H-5), 4.00 (s, 3H, OCH3), 3.97 (s, 3H, OCH3). 13C NMR
(CDCl3) ꢀ 196.2, 153.6, 149.6, 136.1, 135.6, 132.8, 131.7, 131.0, 129.8, 128.7,
128.6, 128.4, 127.3, 126.5, 126.1, 112.8, 110.4, 56.7, 56.7. Found: C, 77.98;
H, 5.84%. C17H18O4 requires: C, 78.06; H, 5.52%.
3,4-Dimethoxy-30-methoxybenzophenone (Run 6): beige crystals
(CH2Cl2/ PE), m.p. 84–85ꢀC. H NMR (CDCl3) ꢀ 7.51 (d, 1H, J ¼ 2.1 Hz,
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H-2), 7.45–7.35 (m, 2H, H-6, H-50), 7.3 (m, 2H, H-20, H-40), 7.14 (ddd, 1H,
J ¼ 8.0, 2.7 and 1.0 Hz, H-60), 6.90 (d, 1H, J ¼ 8.4 Hz, H-5), 3.98 (s, 3H,
OCH3), 3.96 (s, 3H, OCH3), 3.88 (s, 3H, OCH3). 13C NMR (CDCl3) ꢀ 195.9,
160.0, 153.6, 149.5, 140.1, 130.7, 129.7, 126.1, 122.9, 118.8, 114.8, 112.6,
110.3, 56.7, 56.6, 56.0. Found: C, 70.42; H, 6.03%. C17H18O4 requires:
C, 70.57; H, 5.92%.
3,4-Dimethoxy-20-bromobenzophenone (Run 7): white crystals (iPrOH),
m.p. 160–162ꢀC. 1H NMR (CDCl3) ꢀ 7.66 (d, 1H, H-30), 7.60 (d, 1H,