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trans-4-Hydroxystilbenes
2525
concentrated in vacuo. Crude product was crystallized with
Benzene/Hexane; colourless solid; 2a; Yield 1.95 g (92%); m.p. 150ꢀC;
(Lit,[24] m.p. 148ꢀC), IR (KBr): 728, 840, 1168, 1206, 1338, 1578, 1601,
1
1667, 2902, 3033, 3370 cmÀ1. H NMR (Acetone-d6): ꢀ ¼ 3.04 (bs, 1H,
phenolic-OH), 4.27 (s, 2H, CH2), 6.85–6.99 (m, 2H, phenyl-H),
7.13–7.55 (m, 5H, phenyl-H), 7.94–8.02 (m, 2H, phenyl-H). 13C NMR
(Acetone-d6): ꢀ 45.38 (–CH2), 116.01 (þ, 2C, phenyl-C), 127.20 (þ,
phenyl C), 129.13 (þ, 2C, phenyl-C), 129.80 (q, phenyl C), 130.37 (þ,
2C, phenyl-C), 131.89 (þ, 2C, phenyl C), 136.70 (q, phenyl-C), 162.67 (q,
C-OH), 196.17 (q, carbonyl-C); MS (EI, 70 eV) m/z (%) : 212.1 (36, Mþ),
121.1 (100%), 93.1 (25.3), 65.1 (25.2).
2-Phenyl-1-(4-hydroxy-3-methylphenyl)-ethan-1-one (2b).[17] Solid,
benzene–hexane; m.p. 143ꢀC; Yield 95%, IR (KBr): 647, 704, 819,
1021, 1051, 1223, 1334, 1508, 1580, 1667, 3339 cmÀ1
.
1H NMR
(CDCl3): ꢀ 2.27 (s, 3H, CH3), 4.22 (s, 2H, CH2), 5.44 (bs, 1H, OH),
6.77–6.79 (d, 1H, J ¼ 2 Hz, phenyl-H), 7.26–7.31 (m, 5H, phenyl-H),
7.77–7.84 (m, 2H, phenyl-H); Anal. calcd. for C15H14O2 (226): C,
79.64; H, 6.19. Found: C, 79.78; H, 6.28.
2-Phenyl-1-(4-hydroxy-2-methylphenyl)-ethan-1-one
(2c).[17]
Oil,
extracted with CH2Cl2; yield 97%. IR (Neat): 669, 756, 869, 935, 1031,
1219, 1346, 1493, 1596, 1637, 1670, 2926, 3377 cmÀ1. 1H NMR (CDCl3): ꢀ
2.21 (s, 3H, CH3), 4.08 (s, 2H, CH2), 6.51–6.89 (m, 2H, phenyl-H),
7.06–7.25 (m, 6H, phenyl-H and phenolic-OH), 7.27–7.63 (m, 1H,
phenyl-H); Anal. calcd. for C15H14O2 (226): C, 79.64; H, 6.19. Found:
C, 79.80; H, 6.28.
2-Phenyl-1-(4-hydroxy-3-chlorophenyl)-ethan-1-one (2d).[25] Solid,
benzene–hexane, m.p. 164ꢀC; yield 90%. IR (KBr): 565, 649, 704, 818,
1053, 1225, 1349, 1593, 1666, 2368, 3341 cmÀ1; 1H NMR (CDCl3): ꢀ 4.21
(s, 2H, CH2), 6.00 (s, 1H, phenolic-OH), 7.05 (d, 1H, J ¼ 7.02 Hz, phenyl-
H), 7.23–7.36 (m, 5H, phenyl-H), 7.86 (dd, 1H, J ¼ 7.02 Hz, phenyl-H),
8.02 (dd, 1H, J ¼ 1Hz, phenyl-H); Anal. calcd. for C14H11ClO2 (246.5):
C, 68.15; H, 4.46. Found: C, 68.24; H, 4.55.
2-Phenyl-1-(4-hydroxy-2-chlorophenyl)-ethan-1-one
(2e).[25]
Oil,
extracted with CH2Cl2; Yield 97%. IR (Neat): 582, 694, 756, 838, 1036,
1217, 1304, 1599, 1664, 2924, 3022, 3402 cmÀ1. 1H NMR (CDCl3): ꢀ 3.60
(s, 2H, CH2), 5.27 (bs, 1H, phenolic OH), 6.44–6.95 (m, 2H, phenyl-H),
7.01–7.27 (m, 1H, phenyl-H), 7.29–7.51 (m, 5H, phenyl-H); Anal. calcd.
for C14H11ClO2 (246.5): C, 68.15; H, 4.46. Found: C, 68.32; H, 4.50.
2-Phenyl-1-(4-hydroxy-3-methoxyphenyl)-ethan-1-one (2f ). Solid,
EtOAc–hexane; m.p. 109ꢀC (Lit,[24] m.p. 108ꢀC); Yield 90%. IR
(Neat): 559, 757, 804, 1024, 1218, 1435, 1508, 1602, 1672, 2364, 2963,
1
3024, 3406 cmÀ1. H NMR (CDCl3): ꢀ 3.88 (s, 3H, OCH3), 4.18 (s, 2H,