Preparative synthesis of vanillin and vanillal alkanoates

Article abstract of DOI:10.1007/s11167-005-0242-y

Procedures for preparing vanillin and vanillal alkanoates were developed.

Full text of DOI:10.1007/s11167-005-0242-y

Russian Journal of Applied Chemistry, Vol. 78, No. 1, 2005, pp. 120 124. Translated from Zhurnal Prikladnoi Khimii, Vol. 78, No. 1,
2005, pp. 122 126.
Original Russian Text Copyright
2005 by Dikusar, Vyglazov, Moiseichuk, Zhukovskaya, Kozlov.
ORGANIC SYNTHESIS
AND INDUSTRIAL ORGANIC CHEMISTRY
Preparative Synthesis of Vanillin and Vanillal Alkanoates
E. A. Dikusar, O. G. Vyglazov, K. L. Moiseichuk, N. A. Zhukovskaya, and N. G. Kozlov
Institute of Physical Organic Chemistry, Belarussian National Academy of Sciences, Minsk, Belarus
Tereza Inter Limited Liability Company, Moscow, Russia
Received June 16, 2004
Abstract Procedures for preparing vanillin and vanillal alkanoates were developed.
Vanillin (4-hydroxy-3-methoxybenzaldehyde, Ia)
and its homolog, vanillal (4-hydroxy-3-ethoxybenzal-
dehyde, Ib) are widely used in food and perfume
industries [1 3]. Vanillin can also be used as a syn-
thetic precursor of biologically active substances
[4, 5]. However, new processes in food industry de-
mand new aroma chemicals that would have vanilla
smell but be more heat-resistant than vanillin and
stable in a wide range of pH in the presence of en-
zymes. These requirements stimulate chemists to
prepare new vanillin and vanillal derivatives; many of
them appeared to exhibit stronger vanilla smell, com-
pared to the initial compounds, with diverse tints.
a simpler procedure compared to the known routes
[11]. The other esters IIb IIm and IIIb IIIg were
prepared by reactions of Ia and Ib with alkanecarbox-
ylic acid chlorides in the presence of pyridine [15,
16]. To simplify the production process and improve
the purity of the target products for their use in formu-
lations for perfume and food industry, the esters were
also prepared by the Schotten Baumann reaction [9,
17]. The resulting esters IIb IIe and IIIb IIIe
(Tables 1, 2) do not require additional purification.
They are free of benzene and pyridine impurities and
can be directly used in the perfume industry.
The organoleptic assessment of the scents of IIa
IIg and IIIa IIIg was made by the Tasting Council
at the Accredited Checkout and Analytical Laboratory
of the Tereza Inter Limited Liability Company (Mos-
cow, Russia). Esters IIa IIg and IIIa IIIg have
pronounced vanilla smell with various intense tints
(Table 3). Esters IIh IIm have no odor.
Here we report convenient synthetic routes to
vanillin (IIa IIm) and vanillal (IIIa IIIg) esters.
CHO
RO
OC(O)R
EXPERIMENTAL
II a m, III a g
II, R = Me, R = H (a), Me (b), Et (c), Pr (d), Me CH
The IR spectra of the compounds were recorded on
a Protege-460 IR Fourier spectrometer (Nicolet) from
the samples prepared as thin films or KBr pellets; the
UV spectra, on a Specord UV-Vis spectrophotometer
from 1 10 M solutions in 1-butanol; the H NMR
spectra, on a BS-587A spectrometer (100 MHz, Tesla)
2
(e), Bu (f), Me CHCH (g), C H (h), C H (i),
2
2
5
11
6 13
4
C H (j), C H (k), CH Cl (l), 4-MeC H O(CH )
7
15
12 25
2
6
2 2
(m); III, R = Et, R = H (a), Me (b), Et (c), Pr (d),
Me CH (e), Bu (f), Me CHCH (g).
4
1
2
2
2
Some of them were characterized [6 13], but the
lack of some esters in the homologous series of the
vanillin and vanillal derivatives and incompleteness
of the available physicochemical data for the previ-
ously described compounds stimulated us to make this
study, aimed to develop new flavor additives derived
from vanillin and vanillal.
from 5% solutions in CDCl , with octamethyltetracyc-
3
losiloxane as internal reference; and the mass spectra,
on a Chrommas GC/MS Hewlett Packard 5890/5972
gas chromatograph mass spectrometer equipped with
an HP-5MS column, at an ionizing electron energy
of 70 eV.
Alkanecarboxylic acid chlorides were prepared by
refluxing the corresponding carboxylic acids with a
The formates were prepared by the reactions of
vanillin Ia and vanillal Ib with formic acid in the
presence of dicyclohexylcarbodiimide [14], which is
1.5-fold excess of SOCl in benzene.
2
1070-4272/05/7801-0120 2005 Pleiades Publishing, Inc.

PREPARATIVE SYNTHESIS OF VANILLIN AND VANILLAL ALKANOATES
Table 1. Properties of esters IIa IIm and IIIa IIIg
121
Found, %
Calculated, %
M
Yield,
%
Ester
Tm, C
Formula
C
H
C
H
found
calculated
IIa
IIb
IIc
IId*
IIe
70
92
79
81
89
84
84
85
82
77
75
78
76
73
87
84
92
93
92
82
54 55
78 79
35 36
60.08
62.05
63.64
65.12
65.07
66.29
66.27
67.39
68.45
69.18
72.54
52.63
69.02
62.03
63.72
65.07
66.34
66.29
67.41
67.49
4.43
5.43
5.79
6.42
6.46
7.02
7.04
7.41
7.80
8.03
9.37
4.08
5.97
5.28
5.84
6.44
7.07
7.01
7.45
7.41
C9H8O4
C10H10O4
C11H12O4
C12H14O4
C12H14O4
C13H16O4
C13H16O4
C14H18O4
C15H20O4
C16H22O4
C21H32O4
C10H9ClO4
C18H18O5
C10H10O4
C11H12O4
C12H14O4
C13H16O4
C13H16O4
C14H18O4
C14H18O4
60.00
61.85
63.46
64.86
64.86
66.09
66.09
67.18
68.16
69.04
72.38
52.53
68.78
61.85
63.46
64.86
66.09
66.09
67.18
67.18
4.48
5.19
5.77
6.31
6.31
6.83
6.83
7.25
7.63
7.91
9.26
3.97
5.77
5.19
5.77
6.31
6.83
6.83
7.25
7.25
180
194
208
222
222
236
236
250
264
278
348
228
314
194
208
222
236
236
250
250
180.2
194.2
208.2
222.2
222.2
236.3
236.3
250.3
264.3
278.3
348.5
228.6
314.3
194.2
208.2
222.2
236.3
236.3
250.3
250.3
29 30
IIf*
IIg*
IIh*
IIi*
IIj*
IIk
IIl*
IIm
IIIa
IIIb
IIIc
IIId*
IIIe
IIIf*
IIIg*
63 64
47 48
33 34
45 47
45 46
20 20
* T , C (p, mm Hg), d , n : 137 138 (0.5), 1.2101, 1.5281 (IId); 129 130 (I), 1.1807, 1.5273 (IIf); 129 130 (0.5), 1.1825,
m
20
D
1.5235 (IIg); 155 156 (0.5), 1.1228, 1.5068 (IIh); 163 164 (0.5), 1.1033, 1.5092 (IIi); 170 171 (0.5), 1.0949, 1.5079 (IIj);
145 146 (0.5), 1.2009, 1.5272 (IIId); 150 151 (0.5), 1.1129, 1.5213 (IIIf); 132 133 (0.5), 1.0954, 1.5180 (IIIg).
** Cl, %: found 15.39, calculated 15.51 (IIl).
Table 2. 1H, IR, and UV spectra of esters IIa IIm and IIIa IIIg
1
Ester
IIa
1H NMR spectrum, , ppm
IR spectrum, , cm
UV spectrum, max, nm ( )
3.91 s (3H, MeO), 7.20 7.57 m (3H, 3110, 3077, 3060, 3045, 3020, 2995, 2960, 205 (9000), 223 (14000),
C6H3), 8.27
9.95 s (1H, CHO)
s
[1H, OC(O)H],
2928, 2847, 2805, 2749, 1757, 1685, 1801, 260 (8000), 308 (3000)
1473, 1455, 1426, 1392, 1275, 1204, 1197,
1154, 1124, 1097, 1029, 962, 875, 867,
821, 733, 679, 632, 590, 574
IIb
2.32 s (3H, Me), 3.92 s (3H, 3090, 3070, 3055, 3017, 2965, 2945, 2920, 206 (8000), 224 (15000),
MeO), 7.18 d, 7.48 m (3H, C6H3), 2848, 2805, 2755, 1758, 1690, 1599, 1507, 261 (8000), 309 (3000)
9.92 s (1H, CHO)
1471, 1427, 1396, 1377, 1280, 1220, 1209,
1155, 1126, 1033, 1014, 907, 862, 830,
739, 680, 600, 580
IIc
IId
1.25 t (3H, MeCH2), 2.52 q (2H, 3115, 3070, 3017, 2968, 2940, 2875, 2855, 205 (8000), 223 (14000),
CH2), 3.84 s (3H, MeO), 7.13 d, 2800, 2745, 1766, 1700, 1602, 1504, 1466, 260 (8000), 310 (3000)
7.42 m (3H, C6H3), 9.88 s
(1H, CHO)
1423, 1393, 1275, 1180, 1182, 1145, 1120,
1032, 912, 870, 40, 780, 733, 645, 580
1.02 t (3H, Me), 1.63 m (2H,
CH2), 2.51 t (2H, CH2), 3.84 s
3117, 3071, 3015, 2968, 2939, 2874, 2853, 206 (8000), 224 (15000),
2800, 2743, 1765, 1701, 1601, 1503, 1465, 260 (7000), 310 (3000)
(3H, MeO), 7.15 d, 7.40 m (3H, 1423, 1391,1272, 1181, 1145, 1120, 1031,
C6H3), 9.90 (1H, CHO) 913, 865, 840, 780, 733, 647, 582
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 78 No. 1 2005

122
DIKUSAR et al.
Table 2. (Contd.)
1
Ester
IIe
1H NMR spectrum, , ppm
IR spectrum, , cm
UV spectrum, max, nm ( )
1.30 s, 1.40 s, 2.88 s, 2.88 m (7H, 3115, 3075, 3015, 2976, 2940, 2878, 2845, 206 (9000), 223 (15000),
i-Pr), 3.90 s (3H, MeO), 7.21 d, 2800, 2745, 1763, 1701, 1601, 1503, 1468, 261 (7000), 311 (3000)
7.50 m (3H, C6H3), 9.96 s
(1H, CHO)
1423, 1389, 1270, 1202, 1180, 1150, 1121,
1191, 1033, 960, 914, 865, 815, 780, 734,
650, 580, 550
IIf
0.96 t (3H, Me), 1.20 1.90 m [4H, 3074, 3012, 2962, 2936, 2874, 2860, 2736, 206 (7000), 224 (14000),
(CH2)2], 2.62 t (2H, CH2), 3.96 s 1764, 1701, 1601, 1503, 1466, 1423, 1391, 261 (7000), 310 (3000)
(3H, OMe), 7.15 d, 7.38 m (3H, 1371, 1322, 1284, 1272, 1198, 1181, 1149,
C6H3), 9.90 s (1H, CHO)
1119, 1092, 1082, 1032, 964, 913, 866,
835, 781, 733, 645, 585, 548
IIg
IIh
IIi
1.06 d (6H, Me2C), 1.35 2.90 m 3117, 3070, 3010, 2957, 2934, 2870, 2855, 206 (8000), 223 (14000),
(3H, CH and CH2), 3.96 s (3H, 2743, 1766, 1704, 1601, 1503, 1466, 1424, 260 (7000), 310 (3000)
OMe), 7.12 d, 7.42 m (3H, C6H3), 1390, 1322, 1272, 1200, 1145, 1120, 1032,
9.91 s (1H, CHO) 965, 915, 866, 835, 780, 735, 645, 585, 545
0.90 t (3H, Me), 1.12 1.90 m [6H, 3110, 3070, 3010, 2958, 2935, 2872, 2856, 207 (8000), 223 (14000),
(CH2)3], 2.58 m (2H, CH2), 3.88 s 2743, 1765, 1704, 1602, 1503, 1465, 1424, 260 (7000), 311 (3000)
(3H, OMe), 7.13 d, 7.44 m (3H, 1392, 1321, 1271, 1200, 1144, 1120, 1033,
C6H3), 9.95 s (1H, CHO)
965, 915, 867, 835, 781, 736, 645, 585, 544
0.96 t (3H, Me), 1.15 1.88 m [8H, 3109, 3070, 3015, 2958, 2936, 2872, 2857, 207 (7000), 224 (14000),
(CH2)4], 2.51 m (2H, CH2), 3.86 s 2744, 1764, 1704, 1601, 1503, 1464, 1424, 261 (7000), 310 (3000)
(3H, OMe), 7.12 d, 7.45 m (3H, 1390, 1322, 1271, 1201, 1144, 1120, 1032,
C6H3), 9.91 s (1H, CHO)
965, 914, 867, 835, 782, 736, 644, 585, 545
IIj
0.92 t (3H, Me), 1.32 m [8H,
(CH2)4], 1.79 m (2H, CH2), 2.60 m 2746, 1763, 1703, 1602, 1504, 1464, 1424, 262 (7000), 310 (3000)
(2H, CH2), 3.88 s (3H, OMe), 1391, 1323, 1271, 1202, 1145, 1120, 1031,
3108, 3070, 3016, 2957, 2935, 2872, 2856, 208 (7000), 224 (14000),
7.14 d, 7.47 m (3H, C6H3), 9.90 s 965, 915, 867, 834, 782, 735, 644, 585, 544
(1H, CHO)
IIk
IIl
0.89 t (3H, Me), 1.30 m [18H,
CH2)9], 1.75 m (2H, CH2), 2.59 m 2741, 1766, 1703, 1601, 1503, 1466, 1422, 260 (7000), 310 (3000)
3115, 3072, 3015, 2955, 2935, 2870, 2855, 206 (7000), 223 (14000),
(2H, CH2), 3.87 s (3H, OMe),
7.16 d, 7.41 m (3H, C6H3), 9.91 s 964, 915, 866, 835, 780, 734, 645, 585
(1H, CHO)
3.88 s (3H, MeO, 4.39 s (2H,
CH2), 7.24 d, 7.50 m (3H, C6H3), 2845, 2805, 2755, 1770, 1692, 1600, 1507, 261 (7000), 310 (3000)
9.89 s (1H, CHO)
1390, 1325, 1272, 1199, 1145, 1120, 1032,
3095, 3070, 3050, 3015, 2970, 2942, 2922, 208 (8000), 224 (16000),
1471, 1427, 1396, 1377, 1280, 1220, 1209,
1155, 1126, 1033, 1014, 908, 862, 830,
739, 680, 600, 580
IIm
2.28 s (3H, Me), 3.06 t (2H,
3120, 3085, 3032, 3015, 2995, 2933, 2882, 204 (15000), 221 (20000),
CH2O), 3.86 s (3H, OMe), 4.35 t 2857, 2831, 2817, 2790, 2729, 1773, 1704, 260 (7000), 306 (3000)
(2H, CH2C=O), 6.63 7.52 m (7H, 1599, 1511, 1462, 1396, 1376, 1327, 1290,
C6H3 and C6H4), 9.90 s (1H, CHO) 1248, 1209, 1179, 1131, 1042, 1028, 955, 910,
890, 880, 850, 827, 818, 781, 731, 590, 514
IIIa
IIIb
1.46 t (3H, Me), 4.18 q (2H,
CH2), 7.22 d, 7.51 m (3H, C6H3), 2744, 1733, 1698, 1599, 1505, 1439, 1391, 261 (8000), 308 (3000)
8.32 s [1H, OC(O)H], 9.97 s (1H, 1276, 1197, 1160, 1138, 1098, 1040, 895,
3110, 3081, 3015, 2988, 2940, 2840, 2813, 205 (8000), 222 (15000),
CHO)
1.41 t (3H, MeCH2), 2.32 s [3H, 3080, 2982, 2934, 2907, 2880, 2850, 2830, 204 (8000), 224 (15000),
MeC(O)], 4.11 q (2H, CH2), 2736, 1768, 1694, 1600, 1592, 1509, 1479, 261 (8000), 309 (3000)
7.20 d, 7.45 m (3H, C6H3), 9.92 s 1441, 1392, 1370, 1320, 1288, 1273, 1210,
868, 851, 824, 800, 745, 618, 590
(1H, CHO)
1197, 1156, 1040, 1011, 973, 900, 870,
832, 800, 786, 745, 726, 667, 632, 586, 528
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PREPARATIVE SYNTHESIS OF VANILLIN AND VANILLAL ALKANOATES
123
Table 2. (Contd.)
1H NMR spectrum, , ppm
1
Ester
IIIc
IR spectrum, , cm
UV spectrum, max, nm ( )
1.35 m (6H, 2MeCH2), 2.65 q (2H, 3115, 3080, 3055, 2985, 2942, 2890, 2875, 205 (8000), 224 (14000),
CH2C=O), 4.13 q (2H, CH2O), 2840, 2795, 2740, 1760, 1697, 1601, 1589, 261 (8000), 310 (3000)
7.16 q, 7.45 m (3H, C6H3), 9.91 s 1508, 1480, 1465, 1435, 1401, 1380, 1353,
(1H, CHO)
1353, 1324, 1288, 1264, 1206, 1161, 1140,
1115, 1075, 1040, 1007, 973, 890, 872,
826, 800, 784, 585
IIId
1.03 t (3H, Me), 1.42 t (3H,
MeCH2O), 1.64 m (2H, CH2),
2.52 t (2H, CH2), 4.12 q (2H,
MeCH2O), 7.17 d, 7.44 m (3H,
C6H3), 9.92 s (1H, CHO)
3114, 3077, 3055, 2983, 2941, 2890, 2875, 206 (8000), 223 (15000),
2843, 2795, 2740, 1761, 1698, 1600, 1589, 261 (8000), 310 (3000)
1506, 1480, 1465, 1440, 1400, 1381, 1353,
1325, 1288, 1264, 1206, 1160, 1140, 1113,
1075, 1040, 1006, 973, 890, 872, 826, 800,
784, 585
IIIe
IIIf
1.27 d (6H, Me2C), 1.38 t (3H,
Me), 2.78 m (1H, CH), 4.08 q
(2H, CH2), 7.10 d, 7.40 m (3H, 1586, 1508, 1420, 1435, 1400, 1385, 1320,
3120, 3080, 3055, 2990, 2975, 2939, 2895, 204 (8000), 223 (14000),
2880, 2842, 2790, 2740, 1752, 1697, 1600, 261 (7000), 310 (3000)
C6H3), 9.91 s (1H, CHO)
1288, 1262, 1160, 1117, 1099, 1033, 974,
916, 870, 821, 800, 785, 751, 655, 580
1.00 t (3H, Me), 1.20 1.90 m [4H, 3110, 3076, 3055, 2984, 2941, 2891, 2875, 205 (8000), 223 (15000),
(CH2)2], 1.42 t (3H, MeCH2O), 2845, 2795, 2740, 1763, 1698, 1602, 1589, 261 (8000), 310 (3000)
2.61 t (2H, CH2C=O), 4.12 q (2H, 1506, 1480, 1465, 1441, 1402, 1381, 353,
MeCH2O), 7.16 d, 7.43 m (3H,
C6H3), 9.92 s (1H, CHO)
1325, 1288, 1264, 1206, 1161, 1140, 1113,
1075, 1040, 1006, 975, 890, 873, 826, 801,
784, 584
IIIg
1.08 d (6H, Me2C), 1.40 t (3H,
3118, 3070, 3050, 3020, 2963, 2936, 2874, 206 (7000), 224 (15000),
MeCH2O), 1.40 2.85 m (3H, CH and 2834, 2785, 2737, 1764, 1699, 1600, 1503, 261 (8000), 310 (3000)
CH2), 4.11 q (2H, MeCH2O), 1467, 1434, 1391, 1370, 1321, 1280, 1272,
7.12 d, 7.42 m (3H, C6H3), 9.91 s 1180, 1150, 1119, 1092, 1041, 973, 915,
(1H, CHO) 897, 869, 830, 786, 744, 730, 650, 580
Vanillin and vanillal formates IIa and IIIa.
A 0.12-mol portion of 99% formic acid was added to
a solution of 0.1 mol of Ia or Ib and 0.1 mol of dicy-
clohexylcarbodiimide in 500 ml of absolute benzene.
The mixture was stirred and kept at 20 23 C for 24
36 h. The dicyclohexylurea precipitate was filtered off
and washed with 100 ml of benzene; the filtrate was
Table 3. Results of organoleptic assessment of the smell
of esters IIa IIg and IIIa IIIg
Ester
IIa
IIb
IIc
Smell
Vanilla, wood, with powder tint
Vanilla-wood, with clove-spicy tint
Vanilla, honey
washed with water and saturated aqueous NaHCO .
3
IId
IIe
Cream-milk, vanilla
Chocolate-vanilla, cream
The benzene solution was dried over CaCl , the sol-
2
vent was distilled off, and the residue was recrystal-
lized from methanol.
IIf
IIg
Vanilla-rum, with cream tint
Vanilla-rum, with fruit tint
Vanillin and vanillal alkanoates IIb IIm and
IIIb IIIg. A 0.25-mol portion of anhydrous pyridine
was added to a solution of 0.2 mol of vanillin Ia or
vanillal Ib in 500 ml of anhydrous CH Cl , and
IIIa
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
Wood, vanilla, with spicy tint
Vanilla-flower, with honey tint
Vanilla-honey, with wood tint
Cream-vanilla, with baked milk tint
Vanilla-cream, with white chocolate tint
Vanilla-rum, with cream chocolate tint
Vanilla-fruit, with cream-clove tint
2
2
0.2 mol of appropriate alkanecarboxylic acid chloride
was added in small portions, with stirring by shaking
the reaction flask. The mixture was refluxed for 1 h,
the solvent was distilled off by heating on a water
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 78 No. 1 2005

124
DIKUSAR et al.
bath, and the residue was dissolved in 500 ml of ben-
zene, washed three times with water and three times
with 5% aqueous NaHCO , and dried over CaCl .
The solvent was distilled off, and the residue was
distilled in a vacuum (IId, IIf IIj, IIId, IIIf, IIIg)
or recrystallized from benzene hexane (IIb, IIc, IIe,
IIm, IIIb, IIIc, IIIe). In the case of IIk and IIl, the
residue was a noncrystallizing greasy substance.
Intermediates in Production of Perfumes and Cos-
metics: Handbook), Moscow: Agropromizdat, 1990.
2. Shaikh, Y., Specialty Aroma Chemicals in Flavors
and Fragrance, Carol Stream, Illinois: Allured, 2002.
3
2
3. Voitkevich, S.A. and Kheifits, L.A., Ot drevnikh bla-
govonii k sovremennym parfyumerii i kosmetike (From
Ancient Fragrances to Modern Perfumes and Cosmet-
ics), Moscow: Pishchevaya Prom st., 1997.
4. Kozlov, N.G. and Basalaeva, L.I., Zh. Org. Khim.,
The solvents CH Cl and C H distilled from the
2
2
6 6
2003, vol. 39, no. 5, pp. 765 769.
reaction mixture can be reused after distillation from
P O on a Vigreux column.
5. Plemenkov, V.V., Vvedenie v khimiyu prirodnykh
soedinenii (Introduction to Chemistry of Natural Com-
pounds), Kazan, 2001, p. 374.
2
5
Vanillin and vanillal alkanoates IIb IIg and
IIIb IIIg. A 1-mol portion of appropriate alkanecar-
boxylic acid anhydride was added in small portions
with vigorous stirring to a solution of 1 mol of vanil-
lin Ia or vanillal Ib in 1.1 l of 1 N aqueous KOH.
The mixture was stirred for 3 5 h and allowed to
stand for 10 15 h at 20 23 C. Compounds IIb IIg
and IIIb IIIg were isolated by filtration or decanting,
washed with water, and dried in air.
6. Shoenberg, A. and Heck, R.F., J. Am. Chem. Soc.,
1974, vol. 96, no. 25, pp. 7761 7764.
7. King, H., J. Chem. Soc., 1939, nos. 7 9, pp. 1165
1168.
8. Burger, A.P.N., Brandt, E.V., and Koux, D.G., Phyto-
chemistry, 1983, vol. 22, no. 12, pp. 2813 2817.
9. Pisovschi, I.J., Chem. Ber., 1910, vol. 43, no. 8,
pp. 2137 2144.
10. Russel, A., J. Am. Chem. Soc., 1948, vol. 70, no. 3,
CONCLUSION
pp. 1060 1064.
11. Ziegler, G. and Kantlehner, W., Z. Naturforsch. (b),
A procedure was developed for preparing vanillin
and vanillal alkanoates in 70 96% yield. These com-
pounds are of interest as components of flavor food
additives with popular chocolate, caramel, and milk-
cream smells.
2001, vol. 56, no. 11, pp. 1172 1177.
12. Grenier, J.L., Cotelle, N., Cattean, J.P., and Cotelle, P.,
J. Phys. Org. Chem., 2000, vol. 13, no. 9, pp. 511
517.
13. Bohlmann, F. and Zdero, C., Chem. Ber., 1968,
vol. 101, no. 9, pp. 3243 3254.
ACKNOWLEDGMENTS
14. Yuvchenko, A.P., Dikusar, E.A., Zhukovskaya, N.A.,
et al., Zh. Obshch. Khim., 1992, vol. 62, no. 1,
pp. 204 212.
15. Kozlov, N.G., Dikusar, E.A., and Potkin, V.I., Zh.
Prikl. Khim., 2003, vol. 76, no. 1, pp. 107 110.
The study was financially supported by the Bela-
russian Republican Foundation for Basic Research
(project no. Kh 03 079).
16. Dikusar, E.A., Nechai, N.I., Potkin, V.I., et al., Khim.
Prirodn. Soedin., 2003, vol. 39, no. 2, pp. 186 190.
REFERENCES
17. Buehler, C.A. and Pearson, D.E., Survey of Organic
Synthesis, New York: Wiley Interscience, 1970.
Translated under the title Organicheskie sintezy,
Moscow: Mir, 1973, part 2, pp. 290 292.
1. Shulov, L.M. and Kheifits, L.A., Dushistye veshchest-
va i poluprodukty parfyumerno-kosmeticheskogo pro-
izvodstva: Spravochnik (Fragrant Substances and
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 78 No. 1 2005