Molecules 2002, 7
704
OCH2), 6.92 (d, 2H, J=8.5Hz, benzyl Ar-H3), 7.01 (d, 2H, J=8.0Hz, H5), 7.39 (m, 4H, aromatic Hs),
9.84 (s, 1H, CHO); 13C-NMR (CDCl3) δ: 55.5 (benzyl OCH3), 56.2 (OCH3), 70.9 (OCH2), 109.4 (C5),
112.5 (C2), 114.3 (benzyl Ar-C3), 126.8 (C6), 128.0 (benzyl Ar-C1), 129.2 (benzyl Ar-C2), 130.3 (C1),
150.2 (C3), 153.9 (C4), 159.8 (benzyl Ar-C4), 191.2 (CO); MS m/z (relative %): 272 [M+] (3), 122
(10), 121 (100), 91 (5).
3-Methoxy-4-(o-nitrobenzyloxy)benzaldehyde (4c). From 99 mg of 3c, we obtained 4c (88 mg, 85%)
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after chromatography (20% EtOAc/hexanes); Mp: 126-127oC; IR (KBr) cm-1: 1681 (CO); H-NMR
(CDCl3) δ: 4.00 (s, 3H, OCH3), 5.65 (s, 2H, OCH2), 7.01 (d, 1H, J=8.2Hz, H5), 7.44 (dd, 1H, J=1.8,
8.2Hz, H6), 7.48 (d, 1H, J=1.8Hz, H2), 7.53 (t, 1H, J=7.6Hz, benzyl Ar-H4), 7.72 (t, 1H, J=7.6Hz,
benzyl Ar-H5), 7.93 (d, 1H, J=7.9Hz, benzyl Ar-H6) 8.22 (d, 1H, J=8.3Hz, benzyl Ar-H3), 9.86 (s, 1H,
CHO); 13C-NMR (CDCl3) δ: 56.3 (OCH3), 67.9 (OCH2), 109.6 (C5), 112.6 (C2), 125.4 (benzyl Ar-C3),
126.9 (C6), 128.5 (benzyl Ar-C6), 128.8 (benzyl Ar-C4), 131.0 (C1), 133.2 (benzyl Ar-C1), 134.5
(benzyl Ar-C5), 146.9 (C3), 150.3 (C4), 153.1 (benzyl Ar-C2), 191.1 (CO); MS m/z (relative %): 287
[M+] (3), 153 (7), 137 (10), 136 (100), 78 (43).
4-(2,6-Dichlorobenzyloxy)-3-methoxybenzaldehyde (4d). From 166 mg of 3d, we obtained 4d (148
mg, 85%) after chromatography (15% EtOAc/hexanes); Mp: 124-125oC; IR (KBr) cm-1: 1683 (CO);
1H-NMR (CDCl3) δ: 3.90 (s, 3H, OCH3), 5.40 (s, 2H, OCH2), 7.18 (d, 1H, J=8.1Hz, H5), 7.37 (m, 5H,
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aromatic Hs), 9.89 (s, 1H, CHO); C-NMR (CDCl3) δ: 56.4 (OCH3), 66.5 (OCH2), 110.0 (C5), 113.2
(C2), 126.7 (C6), 128.7 (benzyl Ar-C3), 128.9 (benzyl Ar-C2), 130.9 (benzyl Ar-C4), 131.5 (C1), 137.4
(benzyl Ar-C1), 150.6 (C3), 154.0 (C4), 191.2 (CO); MS m/z (relative %): 312 [M++2] (14), 310 [M+]
(20), 161 (67), 159 (100), 123 (7).
4-(3,4-Dichlorobenzyloxy)-3-methoxybenzaldehyde (4e). From 105 mg of 3e, we obtained 4e (93 mg,
85%) after chromatography (15% EtOAc/hexanes); Mp: 113oC (decomposed); IR (KBr) cm-1: 1684
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(CO); H-NMR (CDCl3) δ: 3.97 (s, 3H, OCH3), 5.13 (s, 2H, OCH2), 6.94 (d, 1H, J=8.1Hz, H5), 7.28
(d, 1H, J=8.1Hz, H6), 7.43 (m, 3H, aromatic Hs), 7.55 (s, 1H, H2), 9.85 (s, 1H, CHO); 13C-NMR
(CDCl3) δ: 56.2 (OCH3), 69.6 (OCH2), 109.6 (C5), 112.5 (C2), 126.6(C6 and benzyl Ar-C6), 129.3
(benzyl Ar-C2), 130.8 (C1), 130.9 (benzyl Ar-C5), 132.5 (benzyl Ar-C3), 133.1 (benzyl Ar-C4), 136.4
(benzyl Ar-C1), 150.2 (C3), 153.1 (C4), 191.1 (CO); MS m/z (relative %): 312 [M++2] (9), 310 [M+]
(13), 161 (70), 159 (100), 123 (7).
4-Allyloxy-3-methoxybenzaldehyde (4f). From 268 mg of 3f, we obtained 4f (262 mg, 91%) after
chromatography (20% EtOAc/hexanes); Mp: 24-25oC. Spectral data were identical to those previously
reported [15].