DIKUSAR, KOZLOV
994
nD20 = 1.5810. IR spectrum, ν, cm–1: 3110, 3090, 3080,
3040, 3010 (C–Harom); 1764, 1700 (C=O); 1600, 1499,
1480, 1420, 1390 (C–Carom); 1470 (CH2); 900, 880,
830, 780, 720, 703, 660 (δC–Harom). UV spectrum,
λmax, nm (ε): 210 (15000), 218 (16000), 256 (8000),
(50000), 220 (70000), 258 (39000), 305 (15000).
1H NMR spectrum, δ, ppm: 3.04 s [4H, (CH2)2], 3.84 s
(6H, CH3O), 7.12–7.55 m (6H, C6H3), 9.90 s (2H,
CHO). Found, %: C 62.63; H 5.02. M 372.7. C20H18O8.
Calculated, %: C 62.18; H 4.70. M 386.4.
1
308 (4000). H NMR spectrum, δ, ppm: 3.79 s (CH2),
4-Formyl-2-methoxyphenyl o-chlorobenzoate
(IIIm). Yield 86%, mp 91–92°C. IR spectrum, ν, cm–1:
3095, 3067, 3020 (C–Harom); 1746, 1701, 1686 (C=O);
1600, 1590, 1505, 1468, 1455, 1430, 1421, 1390
(C–Carom); 961, 876, 856, 814, 790, 741, 710, 683, 650,
3.89 s (CH3O), 7.10–7.50 m (C6H3, C6H5), 9.89 s
(CHO). Found, %: C 71.30; H 5.44. C16H14O4.
M 260.1. Calculated, %: C 71.10; H 5.22. M 270.3.
4-Formyl-2-methoxyphenyl 2-phenylbutyrate
(IIIi). Yield 85%, mp 69–70°C. IR spectrum, ν, cm–1:
3113, 3080, 3061, 3040, 3025 (C–Harom); 1756, 1702,
1689 (C=O); 1601, 1501, 1451, 1425, 1396, 1362
(C–Carom); 1467 (CH2); 930, 885, 843, 810, 765, 733,
700, 652 (δC–Harom). UV spectrum, λmax, nm (ε): 210
630, 595 (δC–Harom); 550 (C–Cl). UV spectrum, λmax
,
nm (ε): 208 (27000), 219 (23000), 255 (12000), 304
1
(4000). H NMR spectrum, δ, ppm: 3.90 s (CH3O),
7.15–7.55 m and 8.00–8.25 m (C6H3, C6H4), 9.97 s
(CHO). Found, %: C 62.24; H 4.06; Cl 11.92. M 281.1.
C15H11ClO4. Calculated, %: C 61.98; H 3.81; Cl 12.20.
M 290.7.
1
(16000), 255 (8000), 307 (4000). H NMR spectrum,
3
3
δ, ppm: 1.42 d (CH3, J = 7.4 Hz), 2.88 d (CH2, J =
3
7.4 Hz), 3.38 q (CH, J = 7.4 Hz), 3.79 s (CH3O),
4-Formyl-2-methoxyphenyl p-chlorobenzoate
(IIIn). Yield 84%, mp 98–99°C. IR spectrum, ν, cm–1:
3105, 3093, 3074, 2999 (C–Harom); 1743, 1703 (C=O);
1593, 1501, 1480, 1463, 1422, 1400, 1391 (C–Carom);
958, 873, 858, 847, 817, 780, 748, 730, 678, 637, 588
(δC–Harom); 522 (C–Cl). UV spectrum, λmax, nm (ε):
204 (25000), 220 (21000), 252 (15000), 303 (4000).
1H NMR spectrum, δ, ppm: 3.93 s (CH3O), 7.20–
7.60 m and 8.05–8.25 m (C6H3, C6H4), 9.98 s (CHO).
Found, %: C 62.16; H 4.01; Cl 11.98. M 282.4.
C15H11ClO4. Calculated, %: C 61.98; H 3.81; Cl 12.20.
M 290.7.
6.90–7.45 m (C6H3, C6H5), 9.89 s (CHO). Found, %:
C 72.68; H 6.30. M 283.9. C18H18O4. Calculated, %:
C 72.47; H 6.08. M 298.3.
4-Formyl-2-methoxyphenyl cinnamate (IIIj).
Yield 84%, mp 59–60°C. IR spectrum, ν, cm–1: 3110,
3090, 3025, 3010 (C–Harom); 3060 (=CH); 1738, 1725,
1700, 1688 (C=O); 1636 (C=C); 1600, 1580, 1503,
1470, 1453, 1425, 1391 (C–Carom); 976, 920, 875, 863,
840, 780, 766, 740, 707, 680, 645 (δC–Harom). UV
spectrum, λmax, nm (ε): 206 (32000), 220 (41000), 280
1
(38000). H NMR spectrum, δ, ppm: 3.90 s (CH3O),
7.10–7.90 m (CH=CH, C6H3, C6H5), 9.96 s (CHO).
Found, %: C 72.53; H 5.19. M 273.0. C17H14O4. Cal-
culated, %: C 72.33; H 5.00. M 282.3.
4-Formyl-2-methoxyphenyl o,p-dichlorobenzoate
(IIIo). Yield 87%, mp 102–103°C. IR spectrum, ν,
cm–1: 3095, 3080, 3068, 3040, 3027 (C–Harom); 1746,
1705, 1689 (C=O); 1598, 1584, 1556, 1508, 1470,
1465, 1417, 1392, 1379 (C–Carom); 961, 937, 900,
871, 852, 845, 835, 802, 784, 735, 675, 642, 588
(δC–Harom); 559, 526 (C–Cl). UV spectrum, λmax, nm
4-Formyl-2-methoxyphenyl 3-(p-tolyloxy)propio-
nate (IIIk). Yield 81%, mp 63–64°C. IR spectrum, ν,
cm–1: 3120, 3085, 3032, 3015 (C–Harom); 1773, 1704
(C=O); 1599, 1511, 1396, 1376 (C–Carom); 1462 (CH2);
955, 910, 890, 880, 850, 827, 818, 781, 731, 590
(δC–Harom). UV spectrum, λmax, nm (ε): 204 (15000),
1
(ε): 212 (32000), 255 (15000), 306 (3000). H NMR
spectrum, δ, ppm: 3.90 s (CH3O), 7.00–7.65 m and
7.95–8.55 m (Harom), 9.97 s (CHO). Found, %:
C 55.85; H 3.28; Cl 21.56. M 311.8. C15H10Cl2O4. Cal-
culated, %: C 55.41; H 3.10; Cl 21.81. M 325.1.
1
221 (20000), 260 (7000), 306 (3000). H NMR spec-
trum, δ, ppm: 2.28 s (CH3), 3.06 t (CH2O, 3J = 6.3 Hz),
3
3.86 s (CH3O), 4.35 t (CH2C=O, J = 6.3 Hz), 6.63–
7.52 m (C6H3, C6H4), 9.90 s (CHO). Found, %:
C 69.02; H 5.97. M 303.6. C18H18O5. Calculated, %:
C 68.78; H 5.77. M 314.3.
4-Formyl-2-methoxyphenyl o,p-dichlorophenoxy-
acetate (IIIp). Yield 81%, mp 115–116°C. IR spec-
trum, ν, cm–1: 3106, 3085, 3077, 3055, 3038, 3020
(C–Harom); 1769, 1699, 1686 (C=O); 1600, 1504, 1680,
1425, 1396, 1380 (C–Carom); 1470 (CH2); 960, 946,
923, 862, 840, 823, 801, 751, 735, 716, 697, 680, 648,
Bis(4-formyl-2-methoxyphenyl) succinate (IIIl).
Yield 84%, mp 130–131°C. IR spectrum, ν, cm–1:
3110, 3073, 3050, 3010 (C–Harom); 1756, 1704 (C=O);
1601, 1592, 1508, 1502, 1455, 1424, 1396 (C–Carom);
1472 (CH2); 944, 917, 881, 868, 836, 803, 781, 735,
671, 587 (δC–Harom). UV spectrum, λmax, nm (ε): 204
583 (δC–Harom); 557, 536 (C–Cl). UV spectrum, λmax
,
nm (ε): 206 (27000), 222 (17000), 257 (5000), 280
1
(5000), 295 (5000), 308 (4000). H NMR spectrum, δ,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 41 No. 7 2005