Please do not adjust margins
New Journal of Chemistry
Page 2 of 8
DOI: 10.1039/C7NJ04794K
ARTICLE
DMSO-d /CDCl solvents on a Bruker DRX-400 spectrometer with
tetramethylsilane as internal reference. The elemental analyses (C, 2-hydroxy-5-methyl benzaldehyde; yellow solid; m.p.= 55-57 C; IR
H, N) were obtained from a Carlo ERBA Model EA 1108 analyzer. (KBr)/ υ(cm ): 3200-3500 (O-H, phenol), 2862, 2736 (C-H aldehyde),
Journal Name
6
3
o
-1
1
Electron Ionization Mass (EI-MASS) spectra were recorded on 1651 (C=O, aldehyde), 1590, 1502 (C=C, Ar), 1215 (C-O); H NMR
Agilent Technology (HP) 5973 instrument at an ionization potential (400 MHz, DMSO)/ δ(ppm): 9.40 (s, 1 H, O-H), 9.05 (s, 1 H,
of 70 eV. X-ray powder diffraction (XRD) measurements were aldehyde), 6.77 (s, 1 H), 6.68 (dd, 1 H, J= 8.24 Hz, J= 2.24 Hz), 6.59
1
3
performed using an X’pert diffractometer of Philips Company with (d, 1H, J= 2.41 Hz), 2.11 (s, 3 H); C NMR/ (100 MHz, CDCl )/
3
monochromatized Cu ka radiation. The crystallite sizes of selected δ(ppm): 198.2, 160.5, 135.2, 133.1, 130.3, 119.9, 117.0, 20.1.
samples were estimated using the sherrer method. The samples
o
were characterized with scanning electron microscope (SEM) 2-hydroxy-5-ethyl benzaldehyde; yellow solid; m.p.= 55-57 C; IR
-
1
(
Philips XL 30) with gold coating. The microwave irradiations were (KBr)/ υ(cm ): 3200-3400 (O-H, phenol), 2869 (C-H, aldehyde), 1651
1
carried out in microwave oven specially designed for the organic (C=O, aldehyde), 1610, 1510 (C=C, Ar), 1226 (C-O); H NMR (400
synthesis (Milestone LAVIS 1000 Basic Microwave). Melting points MHz, CDCl )/ δ(ppm): 11.19 (s, 1 H, O-H), 9.90 (s, 1 H, aldehyde),
3
obtained with a Yanagimoto micro melting point apparatus are 7.61 (s, 1 H), 7.34 (d, J=6.2 Hz, 1 H), 7.17 (d, J= 6.2 Hz, 1 H), 2.62 (q,
1
3
uncorrected. The purity determination of the substrates and 2 H, J=8.1 Hz), 1.25 (t, 3 H, J=8.1 Hz); C NMR/ (100 MHz, CDCl )/
3
reaction monitoring were accomplished by TLC on silica-gel δ(ppm): 198.2, 163.0, 135.8, 133.4, 132.0, 120.8, 118.4, 28.2, 15.7.
polygram SILG/UV 254 plates (from Merck Company).
o
2
-hydroxy-5-isopropyl benzaldehyde; yellow solid; m.p.= 63- 65 C;
-1
IR (KBr)/ υ(cm ): 3200-3400 (O-H, phenol), 2871 (C-H, aldehyde),
654 (C=O, aldehyde), 1590, 1501 (C=C, Ar), 1240(C-O); H NMR
General procedure for the synthesis of magnesium oxide
nanostructure
1
1
To prepare Mg(OH)
of 0.1 M were added to the 0.1 M solution of Mg(NO
distillated H O. Then the suspension was ultrasonically irradiated
2
precursor, NaOH solution with concentration (400 MHz, DMSO)/ δ(ppm): 10.98 (s, 1 H, O-H), 9.93 (s, 1 H,
aldehyde), 7.45 (s, 1 H), 7.25 (s, 1 H), 7.08 (d, 1 H, J=2.0 Hz), 4.01
3 2 2
) .6H O in
1
3
(
m,1 H), 2.9 (d, 6 H, J= 7.7 Hz); C NMR/ (100 MHz, CDCl
3
)/ δ(ppm):
2
1
98.2, 161.4, 142.3, 132.8, 127.9, 119.8, 116.8, 34.55, 24.2.
with a high-density ultrasonic probe immersed directly into the
solution. To prepare MgO powders the obtained precipitate was
calcinated at 400 °C in a furnace.
o
2
-hydroxy-5-tertbuthyl benzaldehyde; yellow solid; m.p.= 51- 53 C;
-1
IR (KBr)/ υ(cm ): 3200-3400 (O-H, phenol), 2862 (C-H, aldehyde),
1
1
640 (C=O, aldehyde), 1583, 1502 (C=C, Ar), 1276 (C-O); H NMR
400 MHz, DMSO)/ δ(ppm): 11.13 (s, 1 H, O-H), 9.83 (s, 1 H,
aldehyde), 7.26 (s, 1 H), 7.19 (s, 1 H, Ar), 7.03 (s, 1 H, Ar), 2.34 (s, 9
General procedure for the synthesis of ortho-hydroxy
benzaldehydes under microwave irradiation
Ortho-hydroxy benzaldehyde derivatives were prepared according
to the procedure as following; 80 mmol of dry paraformaldehyde
(
13
H); C NMR/ (100 MHz, CDCl
1
3
)/ δ(ppm): 198.1, 160.3, 144.9, 131.1,
28.7, 120.4, 117.4, 31.5, 25.0.
(2.4 g) was added to a mixture of 12 mmol desired phenol
derivative and 2.5 mmol of MgO nano crystalline (0.1 g). The
resulted mixture was exposed under microwave irradiation with a
power of 650 W. The progress of reaction was monitored by thin
layer chromatography (TLC) developed by n-hexane:ethyl acetate
2
-hydroxy-3, 5-dimethyl benzaldehyde; yellow liquid; b.p.=223-224
o
-1
C; IR (KBr)/ υ(cm ): 3300-3500 (O-H, phenol), 2860, 2736 (C-H,
aldehyde), 1646 (C=O, aldehyde), 1508, 1481 (C=C, Ar), 1263 (C-O);
1
H NMR (400 MHz, DMSO)/ δ(ppm): 11.25 (s, 1 H, O-H), 9.79 (s, 1 H,
(
8:2). After completion of the reaction, 100 mL sulfuric acid (15%
o
aldehyde), 6.98 (d, 1 H, J= 8.0 Hz), 6.80 (d, 1 H, J= 7.6 Hz), 2.38 (s, 6
H); C NMR/ (100 MHz, CDCl )/ δ(ppm): 190.7, 155.9, 135.1, 131.3,
1
w/w) was added to the reaction mixture and heated at 50 C for 15
min. Then, the reaction mixture was cooled to room temperature
and the product was extracted by dichloromethane (2×50 mL). The
organic layer was dried over anhydrous magnesium sulphate; the
resulted solution from filtration was evaporated to obtain the crude
product. In most cases the product was sufficiently pure for further
use; the other products were purified by column chromatography
using n-hexane:ethyl acetate (95:5 to 70:30).
13
3
27.9, 125.0, 120.8, 21.0, 15.9.
2
-hydroxy-3, 5-ditertbuthyl benzaldehyde; yellow solid; m.p.= 53-55
o
-1
C; IR (KBr)/ υ(cm ): 3200-3500 (O-H, phenol), 2868, 2741 (C-H,
aldehyde), 1652 (C=O, aldehyde), 1607, 1506 (C=C, Ar), 1213 (C-O);
1
3
H NMR (400 MHz, CDCl )/ δ(ppm): 11.65 (s, 1 H, OH), 9.88 (s, 1 H,
1
3
aldehyde), 7.60 (s, 1 H), 7.35 (s, 1 H), 1.44 (s, 9 H), 1.34 (s, 9 H);
C
o
NMR/ (100 MHz, CDCl )/ δ(ppm):190.8, 156.0, 135.1, 131.3, 127.9,
125.0, 120.8, 21.0, 15.9.
3
2
-hydroxy-3-methyl benzaldehyde; yellow liquid; b.p.=208 C; IR
-1
(
KBr)/ υ(cm ): 3300-3500 (O-H, phenol), 2854, 2742 (C-H,
1
aldehyde), 1641 (C=O, aldehyde), 1476 (C=C, Ar), 1201 (C-O);. H
NMR (400 MHz, DMSO)/ δ(ppm): 11.32 (s, 1 H, O-H), 9.86 (s, 1 H,
aldehyde), 7.42 (d, 1 H, J= 2.41 Hz), 6.69 (s, 1 H, Ar), 6.45 (d, 1 H, J=
o
2
-hydroxy naphtaldehyde; dusty solid; m.p.= 83-85 C; IR
-1
(
KBr)/υ(cm ): 3300-3500 (O-H, phenol), 2888, 2766 (C-H, aldehyde),
1
1
3
1642 (C=O, aldehyde), 1592, 1464 (C=C, Ar), 1247 (C-O); H NMR
400 MHz, CDCl )/ δ(ppm): 13.18 (s, 1 H, O-H), 10.83(s, 1 H,
aldehyde), 8.36 (s, 1 H), 8.0 (s, 1 H), 7.81 (s, 1 H), 7.63 (s, 1 H), 7.45
(s, 1 H), 7.16 (s, 1 H); C NMR (100 MHz, CDCl )/ δ(ppm): 193.2,
164.9, 139.1, 132.8, 129.5, 129.1, 127.8, 124.5, 119.1, 118.6, 111.2.
2
1
.41 Hz), 2.32 (s, 3 H); C NMR/ (100 MHz, CDCl3)/ δ(ppm): 189.3,
56.3, 135.9, 131.1, 123.6, 120.4, 118.4, 58.9.
(
3
1
3
o
3
2
-hydroxy-4-methyl benzaldehyde; yellow solid; m.p.= 60-62 C; IR
-1
(
(
KBr)/ υ(cm ): 3420-3500 (O-H, phenol), 2980 (C-H aldehyde), 1690
C=O, aldehyde), 1570, 1480 (C=C, Ar), 1270 (C-O); H NMR (400
1
o
2
, 3-dihydroxy benzaldehyde; gray solid; m.p.= 106-108 C; IR (KBr)/
3
MHz, CDCl )/ δ(ppm): 9.95 (s, 1 H, O-H), 8.9 (s, 1 H, aldehyde), 7.17
-1
υ(cm ): 3200-3400 (O-H, phenol), 2875, 2723 (C-H, aldehyde), 1653
(C=O, aldehyde), 1585, 1484 (C=C, Ar), 1233 (C-O); H NMR (400
3
)/ δ(ppm): 11.10 (s, 1 H, O-H), 9.91 (s, 1 H, aldehyde),
.19 (dd, 2 H, J=15.6 Hz, J=7.6 Hz), 6.96 (d, 1 H, J=7.2 Hz), 5.69 (s, 1
(
2
d, 1 H, J= 2.41 Hz), 7.01 (d, 1 H, J= 8.24 Hz), 6.80 (d, 1 H, J= 2.41 Hz),
1
1
3
3
.60 (s, 3 H); C NMR/ (100 MHz, CDCl )/ δ(ppm): 196.7, 162.6,
MHz, CDCl
7
149.3, 132.8, 124.9, 119.5, 117.2, 21.3.
2
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins