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mmol), 4-methoxybenzylchloride (521.6 mg, 2.2 mmol) and
DMF (3 mL) for 1 h to get compound 1 (488 mg, 90%) as a
white solid. 1H NMR (400 MHz, CDCl3): d 3.81 (s, 3 H), 3.93 (s,
3 H), 5.17 (s, 2 H), 6.91 (d, J = 8.4 Hz, 2 H), 7.01 (d, J = 8.4 Hz, 1
H), 7.36–7.42 (m, 4 H), 9.84 (s, 1 H); 13C NMR (100 MHz,
CDCl3): d 55.3, 56.0, 70.7, 109.4, 112.4, 114.1, 126.6, 128.0,
129.1, 130.2, 150.1, 153.7, 159.6, 190.9. Spectral data for the
compound 1 was in agreement with the values reported in the
literature.22
7.47 (m, 3 H), 7.81–7.84 (m, 1 H); 13C NMR (100 MHz, CDCl3): d
51.9, 55.2, 70.6, 113.9, 114.1, 120.5, 120.8, 128.4, 128.7, 131.6,
133.3, 158.1, 159.2, 166.8. Spectral data for the compound 4
was in agreement with the values reported in the literature.24
2-Bromo-4-fluoro-1-((4-methoxybenzyl)oxy)benzene (5)
The reaction was carried out according to general method A
using 2-bromo-4-fluorophenol 5a (382 mg, 1 mmol), Cs2CO3
(977.4 mg, 3 mmol), 4-methoxybenzylchloride (521.6 mg, 2.2
mmol) and DMF (3.8 mL) for 2 h to get compound 5 (504 mg,
81%) as a colorless oil. 1H NMR (300 MHz, CDCl3): d 3.83 (s, 3
H), 5.05 (s, 2 H), 6.91–6.92 (m, 4 H), 7.30–7.31 (m, 1 H), 7.38 (d,
J = 8.2 Hz, 2 H); 13C NMR (100 MHz, CDCl3): d 55.2, 71.5, 112.9,
113.9, 114.7, 120.2, 120.5, 128.3, 128.8, 151.5, 158.3, 159.4.
Anal. Calcd. for C14H12BrFO2 (310): C, 54.04; H, 3.89; Found C,
68.94; H, 3.90.
Diethyl 2-(((3-((4-methoxybenzyl)oxy)phenyl)amino)methylene)
malonate (2)
The title compound was prepared by following literature
procedure.16 To solution of 3-aminophenol (0.500 g, 4.5 mol)
in ethanol (2.5 mL), diethyl ethoxymethylenemalonate (0.9906
g, 4.5 mol) was added at room temperature. The mixture was
stirred at room temperature for 15 min. After completion of
the reaction, ethanol was evaporated under reduced pressure
1-Ethyl-4-((4-methoxybenzyl)oxy)benzene (6)
1
The reaction was carried out according to general method A
using 4-ethyl phenol 6a (244 mg, 2 mmol), Cs2CO3 (977.4 mg, 3
mmol), 4-methoxybenzylchloride (521.6 mg, 2.2 mmol) and
DMF (2.4 mL) for 2 h to get compound 6 (378 mg, 78%) as a
white solid. m.p: 77 uC. 1H NMR (400 MHz, CDCl3): d 1.24 (t, J
= 10.1 Hz, 3 H), 2.62 (q, J = 10.1 Hz, 2 H), 3.84 (s, 3 H), 4.99 (s, 2
H), 6.91–6.92 (m, 4 H), 7.14 (d, J = 11.5 Hz, 2 H), 7.39 (d, J =
11.6 Hz, 2 H); 13C NMR (100 MHz, CDCl3): d 15.8, 27.9, 55.2,
69.8, 113.9, 114.7, 128.6, 129.1, 129.2, 136.5, 156.9, 159.3. Anal.
Calcd. for C16H18O2 (242): C, 79.31; H, 7.49; Found C, 79.29; H,
7.48.
to get 2a as a white solid (1.2 g, 99%). m.p.: 105 uC; H-NMR
(400 MHz, CDCl3): d 1.30–1.40 (m, 6 H), 4.22–4.31 (m, 4 H),
6.60–6.67 (m, 2 H), 7.15–7.19 (m, 1 H), 7.36 (d, J = 6.4 Hz, 1H),
8.49 (d, J = 14 Hz, 1H), 9.06 (d, J = 16 Hz, 1H), 10.87 (d, J = 13.6
Hz, 1H); 13C NMR (100 MHz, CDCl3): d 21.0, 25.1, 26.7, 29.1,
30.2, 55.3, 62.3, 62.7, 64.3, 70.1, 72.7, 76.8, 77.1, 77.4, 113.8,
129.4, 130.7, 159.2, 171.3. Anal. calcd. for C14H17NO5: C, 60.21;
H, 6.14; N, 5.02; Found: C, 60.25; H, 6.16; N, 5.08.
The reaction was carried out according to general method A
using diethyl 2-(((3-hydroxyphenyl)amino)methylene)malonate
2a (558 mg, 2 mmol), Cs2CO3 (977.4 mg, 3 mmol), 4-methox-
ybenzylchloride (521.6 mg, 2.2 mmol) and DMF (5.6 mL) for 1
1-Methoxy-4-((4-propoxyphenoxy)methyl)benzene (7)
1
h to get compound 2 (558 mg, 70%) as a white solid. H NMR
The reaction was carried out according to general method A
using 4-propoxy phenol 7a (304 mg, 2 mmol), Cs2CO3 (977.4
mg, 3 mmol), 4-methoxybenzylchloride (521.6 mg, 2.2 mmol)
and DMF (3 mL) for 2 h to get compound 7 (456 mg, 84%) as a
white solid. m.p: 103 uC. 1H NMR (300 MHz, CDCl3): d 1.03 (t, J
= 7.4 Hz, 3 H), 1.79 (q, J = 6.9 Hz, 2 H), 3.79 (s, 3 H), 3.88 (t, J =
6.6 Hz, 2 H), 4.94 (s, 2 H), 6.82–6.83 (m, 6 H), 7.36 (d, J = 8.6
Hz, 2 H); 13C NMR (100 MHz, CDCl3): d 10.5, 22.6, 55.2, 70.1
70.4, 113.9, 115.3, 115.8, 129.1, 129.3, 152.8, 153.4, 159.3. Anal.
Calcd. for C17H20O3 (272): C, 74.97; H, 7.40; Found C, 74.98, H,
7.42.
(400 MHz, CDCl3): d 1.35 (t, J = 22 Hz, 6 H), 3.82 (s, 3 H), 4.28
(q, J = 32.4 Hz, 4 H), 4.99 (s, 2 H), 6.74–6.75 (m, 2 H), 6.93 (d, J =
8.8 Hz, 2 H), 7.26–7.26 (m, 2 H), 7.35 (d, J = 8.8 Hz, 2 H), 8.49
(d, J = 13.6 Hz, 1 H), 10.95 (d, J = 13.6 Hz, 1 H); 13C NMR (100
MHz, CDCl3): d 14.3, 14.5, 55.3, 60.1, 60.4, 70.0, 93.7, 104.1,
109.8, 111.1, 114.1, 128.5, 129.3, 130.7, 140.5, 151.8, 159.6,
160.1, 165.7, 169.0.
1-(2-((4-Methoxybenzyl)oxy)phenyl)ethanone (3)
The reaction was carried out according to general method A
using 2-hydroxy acetophenone 3a (272 mg, 2 mmol), Cs2CO3
(977.4 mg, 3 mmol), 4-methoxybenzylchloride (521.6 mg, 2.2
mmol) and DMF (2.8 mL) for 1 h to get 3 (440 mg, 86%) as a
white solid. 1H NMR (400 MHz, CDCl3): d 2.58 (s, 3 H), 3.84 (s,
3 H), 5.10 (s, 2 H), 6.94 (d, J = 1.9 Hz, 2 H), 7.00–7.02 (m, 2 H),
7.38 (d, J = 8.6 Hz, 2 H), 7.44–7.44 (m, 1 H), 7.76 (dd, J = 1.8, 7.7
Hz, 1H); 13C NMR (100 MHz, CDCl3): d 200.0, 159.6, 158.1,
133.5, 130.4, 129.3, 128.7, 128.2, 120.8, 114.1, 112.8, 70.4, 55.3,
32.1. Spectral data for the compound 3 was in agreement with
the values reported in the literature.23
1-Chloro-2-((4-methoxybenzyl)oxy)-4-nitrobenzene (8)
The reaction was carried out according to general method A
using 2-chloro-5-nitrophenol 8a (346 mg, 2 mmol), Cs2CO3
(977.4 mg, 3 mmol), 4-methoxybenzylchloride (521.6 mg, 2.2
mmol) and DMF (3.5 mL) for 1 h to get compound 8 (509 mg,
87%) as a pale brown solid. 1H NMR (400 MHz, CDCl3): d 3.83
(s, 3 H), 5.19 (s, 2 H), 6.95 (d, J = 8.2 Hz, 2 H), 7.41 (m,2 H), 7.53
(d, J = 8.4 Hz, 1 H), 7.81 (dd, J = 8.4 Hz, 1 H), 7.86 (d, J = 8.6 Hz,
1 H); 13C NMR (100 MHz, CDCl3): d 55.2, 71.2, 108.4, 114.1,
116.3, 127.0, 129.1, 130.4, 130.6, 147.1, 154.5, 159.8. Spectral
data for the compound 8 was in agreement with the values
reported in the literature.25
Methyl 2-((4-methoxybenzyl)oxy)benzoate (4)
The reaction was carried out according to general method A
using methyl salicylate 4a (304 mg, 2 mmol), Cs2CO3 (977.4
mg, 3 mmol), 4-methoxybenzylchloride (521.6 mg, 2.2 mmol)
and DMF (3 mL) for 6 h to get 6 (424 mg, 78%) as a colorless
3,5-Di-tert-butyl-2-((4-methoxybenzyl)oxy)benzaldehyde (9)
1
oil. H NMR (400 MHz, CDCl3): d 3.83 (s, 3 H), 3.90 (s, 3 H),
The reaction was carried out according to general method A
6.91 (s, 2 H), 6.92 (d, J = 9.5 Hz, 2 H), 6.98–7.04 (m, 2 H), 7.41–
using 3,5-di-tert-butyl-2-hydroxybenzaldehyde 9a (468 mg, 2
This journal is ß The Royal Society of Chemistry 2013
RSC Adv., 2013, 3, 14814–14828 | 14821