Silica gel supported jones reagent (SJR): A simple, versatile, and efficient reagent for oxidation of alcohols in non-aqueous media

Article abstract of DOI:10.1081/SCC-100106049

Oxidation of alcohols to carbonyl compounds has been carried out by utilization of Jones reagent supported on silica gel (SJR). The SJR procedure has advantages over traditional Jones oxidation procedure. This procedure is safer to carry out and simplified workup by allowing organic media.

Full text of DOI:10.1081/SCC-100106049

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SILICA GEL SUPPORTED JONES REAGENT (SJR): A
SIMPLE, VERSATILE, AND EFFICIENT REAGENT FOR
OXIDATION OF ALCOHOLS IN NON-AQUEOUS MEDIA
Mohammed Hashmat Ali a & Candace J. Wiggin a
a Department of Chemistry, Southeast Missouri State University, Cape Girardeau,
Missouri, 63701, U.S.A.
Version of record first published: 20 Aug 2006.
To cite this article: Mohammed Hashmat Ali & Candace J. Wiggin (2001): SILICA GEL SUPPORTED JONES REAGENT
(SJR): A SIMPLE, VERSATILE, AND EFFICIENT REAGENT FOR OXIDATION OF ALCOHOLS IN NON-AQUEOUS MEDIA, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry, 31:21, 3383-3393
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SYNTHETIC COMMUNICATIONS, 31(21), 3383–3393 (2001)
SILICA GEL SUPPORTED JONES
REAGENT (SJR): A SIMPLE,
VERSATILE, AND EFFICIENT
REAGENT FOR OXIDATION
OF ALCOHOLS IN NON-
AQUEOUS MEDIA
MohammedHashmat Ali *
andCandace J. Wiggin
Department of Chemistry, Southeast
Missouri State University, Cape Girardeau,
Missouri 63701, USA
ABSTRACT
Oxidation of alcohols to carbonyl compounds has been car-
ried out by utilization of Jones reagent supported on silica gel
(SJR). The SJR procedure has advantages over traditional
Jones oxidation procedure. This procedure is safer to carry
out and simplified workup by allowing organic media.
Chromium (VI) compounds are very effective in oxidizing alcohols to
the corresponding carbonyl compounds. Among various Cr (VI) based oxi-
dizing agents, Jones reagent is powerful and is capable of oxidizing almost
any oxidizable organic compound or functional group.1 Jones reagent has
*Corresponding author.
3383
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

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ALI AND WIGGIN
not been widely used in organic synthesis due to the toxicity associated with
the reagent and its by-product. Some of the disadvantages associated with
using Jones reagent are the potential health hazards from handling this
reagent, problems in disposal of the toxic chromium compounds, and diffi-
culty in product isolation. Recently, interest has been shown in utilization of
solid-supported chromium reagents in oxidation reactions.2 Solid supported
chromium reagents have shown promise in circumventing many of the prob-
lems associated with the conventional reaction conditions for Jones reagent
which utilize acetone–water as the reaction media. Solid supported chro-
mium reagents offer advantages over the conventional methods in areas
such as efficiency, selectivity and product isolation. Two methods have
been reported for preparation of solid-supported chromium reagents:
co-grinding CrO3 with a solid support3 and deposition of CrO3 on a solid
support by removal of the solvent from a mixture of the solid support and a
solution of the chromium reagent.4–12 These methods suffer from a number
of disadvantages: cumbersome preparation,7–10 light and moisture sensitiv-
ity,4–6,10 loss of activity upon storing,3,4,6 the necessity of activation by
heating at a high temperature for prolonged period of time,3–6,8 slow reac-
tion,5,10,12 and poor yields.3–5,8 Also, the possibility of coming into contact
with the toxic chromium reagent during preparation and use has hindered
wide acceptance of these chromium-based oxidizing reagents. Thus, an effi-
cient chromium reagent that is simpler and safer to prepare and use will
benefit organic chemists.
In the course of our investigation of reactions on solid support,13–17 we
have developed a novel-oxidizing reagent: silica gel supported Jones
Reagent (SJR). This reagent has been found to affect oxidation of a
number of functional groups, including alcohol.17
Preparation of SJR is very simple: a measured amount of Jones
reagent and flash chromatography grade silica gel are mixed in a flash. It

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takes only a few minutes to prepare the reagent and does not require activa-
tion prior to using. SJR is much safer to prepare and use than existing
chromium reagents. SJR can be prepared just before the reaction is carried
out so there is no need for storing the reagent. However, in contrast to the
earlier reports that chromic acid adsorbed on a solid support remains active
only for one to two weeks if stored under vacuum in the dark,4,6 we found
that the SJR remains active over several months under ambient con-
ditions.18 Another big advantage of our procedure is that the amount of
Jones reagent present on the silica gel may be controlled precisely. For other
supported chromium reagents reported in the literature, the amount of
chromium reagent loaded on the solid support has to be determined by
titration. According to the procedure reported in this paper, a heteroge-
neous mixture of SJR and alcohol in methylene chloride solvent is stirred
to achieve oxidation. (See the experimental for detail procedure). After the
reaction is complete, the reaction mixture is filtered to remove silica gel
along with the chromium compounds absorbed on it. The solid residue is
washed with 60–75 mL of methylene chloride. Methylene chloride is not the
only solvent that can be used in this reaction. We have found that the
oxidation reactions work well in a non-polar solvent such as hexane.
However, if hexane is used as the reaction media a polar solvent such as
ethyl acetate or methylene chloride should be used to wash the solid residue
in order to obtain good yields. The products obtained after the solvent is
removed are often pure by NMR and TLC and do not require further
purification. However, impure products were purified by radial chromato-
graphy using a mixture of ethyl acetate and hexane as the eluent. Oxidation
reaction of alcohols with the SJR reported here are very fast, almost
instantaneous at room temperature, and produces excellent yield of
carbonyl product. SJR is very effective in oxidizing a wide variety of
secondary alcohols with various degree of complexities to the corresponding
ketones and primary alcohols to aldehydes. Alcohol functional groups
are oxidized selectively to the corresponding ketones in the presence of
carbon-carbon multiple bonds 2g. Oxidation of benzoin 1m and 1,2-diphe-
nyl-1,2-ethanediol 1q produced benzaldehyde in significant amount or as the
only product. These results are similar to the report on oxidation of
a-hydroxy carbonyl and 1,2-diols reported in the literature.19,20 Our
attempts to oxidize primary alcohols to aldehydes were met with limited
success. Primary alcohols containing more than sixcarbons ( 1s–1u)
produced good yield of aldehydes. Oxidation of alcohols containing less
than sixcarbons was not clean and failed to produce acceptable yields of
carbonyl compounds. The filtrate collected, after the reaction was complete,
was orange in color and indicated the presence of chromium reagent in it.
We believe, solubility of Jones reagent in low molecular weight alcohols and

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ALI AND WIGGIN
Table. Oxidation of Secondary Alcohols to the Ketones
(continued )

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3387
Table. Continued
(continued )

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ALI AND WIGGIN
Table. Continued
in carbonyl compounds complicated the reaction and also is responsible for
the lower yields. Oxidation of low molecular weight secondary alcohols
(C2–C4) also suffered from similar drawback. The bulkiness of the alcohol
does not affect the efficacy of this reagent. The use of SJR eliminates
or minimizes a number of problems associated with the classical Jones
oxidation reaction including formation of an insoluble semi-solid chromium

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(III) salt by-product. We have found that SJR is superior to the previously
reported chromium reagents on solid supports in terms of ease of prepara-
tion, selectivity and efficiency. Utilization of SJR in the oxidation of
alcohols has made product isolation and disposal of waste easier. Very
little handling of the chromium reagent is involved during the preparation
of SJR. Also, aqueous work-up and extraction of product from the aqueous
media are eliminated. Therefore concerns for users coming in contact with
the toxic chromium reagents are minimized. In this procedure, a small
amount of easy to dispose, solid waste is generated. Therefore, this newly
developed silica gel supported Jones reagent is safer to use and generate
lesser amounts of toxic waste.
EXPERIMENTAL
All reaction mixtures were stirred using Teflon coated magnetic
stirring bars. Methylene chloride was used as received from the supplier
without any further purification. Alcohols utilized in this study were
purchased from Aldrich, Lancaster and Acros Chemical Company. The
alcohols were used as they were received without further purification. All
products were known compounds and were identified by comparison of the
NMR and IR data with those reported in the literature or of authentic
commercial products. Jones reagent was prepared according to the
procedure in ref. 1. The silica gel, used as solid support, was MN-
Kieselgel 60 (0.04–0.063 mm mesh size) supplied by Fisher Scientific.
Proton NMR spectra were recorded on a Bruker DPX-300 NMR instru-
ment. Samples for NMR were dissolved in CDCl3. Proton chemical shifts
are expressed as ppm relative to tetramethylsilane. IR spectra were recorded
on a Perkin–Elmer Spectrum 1000 FT-IR instrument and are reported
in wave numbers (cmꢀ1). Chromatographic separations were carried out
by preparative centrifugal thin-layer chromatography with silica gel
(Merck #7749) on a Chromatotron Model 7924T. Analytical thin-layer
chromatography was done on pre-coated silica gel plates with 254 nm fluor-
escent indicator (Merck #5715) and developed in ethyl acetatehexanes (1 : 4)
mixed solvent system. Compounds were visualized by a UV lamp and/or by
staining either with p-anisaldehyde/sulfuric acid or phosphomolybdic acid.
General Procedure
A 100 mL round bottom flask fitted with a rubber septum was charged
with 5 gm flash chromatographic grade silica gel. 1.5 mL of Jones reagent

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ALI AND WIGGIN
(12 mmols) was added drop-by-drop using a syringe while the content of the
flask was stirred using a magnetic stirring bar. After the addition of the
Jones reagent was complete, stirring of the silica gel continued until a free
flowing orange solid was obtained, which took less than 5 min. 25 mL of
methylene chloride was then added to the flask and the heterogeneous mix-
ture was stirred. A solution of the alcohol (3–4 mmoles) in about 2 mL of
methylene chloride was then added to the reaction mixture. The orange
color of the supported reagent turned dark immediately upon addition of
the alcohol solution. After stirring for 5 min the reaction mixture was fil-
tered through a sintered-glass funnel. The solid was washed with about
75 mL of methylene chloride. Removing the solvent from the combined
methylene chloride solutions isolated products. The isolated products were
often pure by proton NMR and TLC. Impure products were purified by
employing radial chromatography using a 1 : 9 mixture of ethyl acetate and
hexane as the eluent.
2-Pentanone (2a)21 1H NMR (300 MHz, CDCl3) 0.94 (t, j ¼ 6.5 Hz,
3H), 1.60 (m, 2H), 2.13 (s, 3H), 2.41 (t, J ¼ 7.20 Hz, 2H); 13C NMR 13.44,
17.06, 29.61, 45.42, 108.92; IR (neat) 734, 918, 963, 1170, 1237, 1272, 1365,
1410, 1459, 1715, 2877, 2937, 2965 cmꢀ1
.
3-Pentanone (2b)21 1H NMR (300 MHz, CDCl3) 1.05 (t, j ¼ 7.4 Hz,
6H), 2.43 (q, j ¼ 7.4 Hz, 4H); 13C NMR 7.60, 35.20, 211.90; IR (neat) 734,
812, 918, 956, 1094, 1122, 1171, 1358, 1377, 1415, 1460, 1716, 2884, 2908,
2940, 2979 cmꢀ1
.
2-Hexanone (2c)21 1H NMR (300 MHz, CDCl3) 0.90 (t, j ¼ 7.2 Hz,
3H), 1.33 (m, 2H), 1.57 (m, 2H), 2.15 (s, 3H), 2.44 (t, j ¼ 7.5 Hz, 2H);
13C NMR 13.45, 22.00, 25.62, 29.43, 43.17, 209.89; IR (neat) 590, 801,
881, 1050, 1089, 1170, 1261, 1368, 1410, 1456, 1712, 2876, 2934, 2967 cmꢀ1
.
4-Methyl-2-pentanone (2d)21 1H NMR (300 MHz, CDCl3) 0.93 (d,
j ¼ 6.7 Hz, 6H), 2.12 (s, 3H), 2.05–2.17 (m, 1H), 2.31 (d, j ¼ 6.95, 2H);
13C NMR 22.61 (2C), 24.67, 30.36, 52.79, 208.6; IR (neat) 649, 732, 911,
1170, 1242, 1367, 1467, 1710, 2873, 2935, 2961 cmꢀ1
.
2-Octanone (2e)21 1H NMR (300 MHz, CDCl3) 0.88 (t, j ¼ 6.6 Hz, 3H),
1.30 (m, 6H), 1.58 (m, 2H), 2.14 (s, 3H), 2.43 (t, j ¼ 7.4 Hz, 2H); 13C NMR
14.14, 22.60, 23.90, 28.96, 29.81, 31.73, 43.80, 209.13; IR (neat) 719, 946,
1035, 1114, 1165, 1225, 1277, 1361, 1411, 1466, 1717, 2858, 2930, 2957 cmꢀ1
.
Cyclopentanone (2f)21 1H NMR (300 MHz, CDCl3) 1.97 (m, 4H), 2.15
(m, 4H); 13C NMR 23.28, 38.36, 220.54; IR (neat) 741, 833, 913, 959, 1047,
1152, 1231, 1267, 1312, 1407, 1454, 1746, 2884, 2966 cmꢀ1
.
4-Ethyl-1-octyn-3-one (2g)21 1H NMR (300 MHz, CDCl3) 0.89 (t,
j ¼ 7.1 Hz, 3H), 0.90 (t, j ¼ 7.4 Hz, 3H), 1.20–1.35 (m, 4H), 1.40–1.80
(m, 4H), 2.43 (m, 1H), 3.26 (s, 1H); 13C NMR 11.57, 13.89, 22.70, 24.26,
29.33, 30.50, 56.04, 78.93, 80.67, 191.68; IR (neat) 741, 813, 896, 1020, 1072,

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3391
1188, 1266, 1382, 1422, 1460, 1676, 1719, 2093, 2861, 2874, 2934, 2963,
3293 cmꢀ1
.
Cyclohexanone (2h)21 1H NMR (300 MHz, CDCl3) 1.74 (m, 2H), 1.86
(m, 4H), 2.35 (m, 4H); 13C NMR 25.03, 27.09 (2C), 41.99 (2C), 211.94; IR
(neat) 652, 749, 864, 908, 1017, 1118, 1221, 1311, 1338, 1422, 1449, 1714,
2863, 2938 cmꢀ1
.
2-Methylcyclohexanone (2i)21 1H NMR (300 MHz, CDCl3) 1.03 (d,
j ¼ 6.6 Hz, 3H), 1.36 (m, 1H), 1.64 (m, 2H), 1.83 (m, 1H), 2.07 (m, 2H),
2.30–2.43 (m, 3H); 13C NMR 14.74, 25.22, 28.01, 36.23, 41.88, 45.38, 213.55;
IR (neat) 647, 732, 816, 865, 918, 990, 1052, 1155, 1215, 1313, 1376, 1428,
1449, 1722, 2861, 2927 cmꢀ1
.
3-Methylcyclohexanone (2j)21 1H NMR (300 MHz, CDCl3) 1.02 (d,
j ¼ 6.2 Hz, 3H), 1.37 (m, 1H), 1.64–1.70 (m, 1H), 1.84–2.10 (m, 4H),
2.20–2.41 (m, 3H); 13C NMR 22.06, 25.32, 33.28, 34.21, 41.09, 49.96,
211.62; IR (neat) 751, 817, 866, 960, 1055, 1116, 1224, 1275, 1317, 1344,
1360, 1421, 1456, 1715, 2870, 2928, 2955 cmꢀ1
.
4-Methylcyclohexanone (2k)21 1.02 (d, j ¼ 6.20 Hz, 3H), 1.36–1.50 (m,
2H), 1.82–2.10 (m, 3H), 2.29–2.40 (m, 4H); 13C NMR 20.42, 30.53, 34.22,
40.20, 211.03; IR (neat) 745, 908, 957, 1003, 1122, 1184, 1248, 1331, 1421,
1459, 1717, 2870, 2929, 2955 cmꢀ1
.
4-tert-Butylcyclohexanone (2l)21 1H NMR (300 MHz, CDCl3) 0.91 (s,
9H), 1.39–1.51 (m, 4H), 2.03–2.12 (m, 1H), 2.26–2.40 (m, 4H); 13C NMR
27.61, 32.46, 41.30, 46.70, 212.46; IR (neat) 667, 703, 737, 841, 944, 1162,
1219, 1332, 1366, 1420, 1449, 1471, 1718, 2870, 2911, 2954 cmꢀ1
.
Benzil (2m)21 1H NMR (300 MHz, CDCl3) 7.50 (m, 4H), 7.63 (m, 2H),
7.96 (m, 4H); 13C NMR 128.87, 129.69, 132.76, 134.78, 194.23; IR (film)
683, 717, 795, 875, 998, 1071, 1172, 1210, 1323, 1450, 1579, 1594, 1658, 3029,
3064 cmꢀ1
.
(d, l)-Menthone (2n)21 1H NMR (300 MHz, CDCl3) 0.86 (d, J ¼ 6.7 Hz,
3H), 0.91 (d, J ¼ 6.7 Hz, 3H), 1.01 (d, J ¼ 6.2 Hz, 3H), 1.34–1.40 (m, 2H),
1.80–2.2 (m, 6H), 2.18–2.37 (m, 1H) ppm; 13C NMR 18.72, 21.22, 22.31,
25.92, 27.90, 33.96, 35.50, 50.87, 55.83, 212.09 ppm; IR (film) 608, 747, 866,
994, 1044, 1093, 1117, 1155, 1246, 1286, 1367, 1457, 1711, 2871, 2928,
2956 cmꢀ1
.
(d, l)-Camphor (2o)21 1H NMR (300 MHz, CDCl3) 0.84 (s, 3H), 0.91
(s, 3H), 0.96 (s, 3H), 1.13–1.47 (m, 2H), 1.60–1.73 (m, 1H), 1.85 (d,
j ¼ 18.3 Hz, 1H), 1.90–1.98 (m, 1H), 2.09 (t, j ¼ 4.5 Hz, 1H), 2.30–2.40 (dt,
j ¼ 3.84, 18.3 Hz, 1H); 13C NMR 9.26, 19.15, 19.78, 27.05, 29.90, 43.03,
43.29, 46.78, 57.69, 219.66; IR (film) 646, 748, 851, 944, 1020, 1044, 1092,
1276, 1322, 1372, 1390, 1416, 1447, 1742, 2873, 2960 cmꢀ1
.
Benzophenone (2p)22 1H NMR (300 MHz, CDCl3) 7.44 (m, 2H),
7.51–7.57 (m, 1H), 7.78 (m, 2H); 13C NMR 128.23, 129.98, 132.37, 137.52,

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ALI AND WIGGIN
196.60; IR (film) 638, 697, 763, 810, 919, 941, 999, 1028, 1074, 1150, 1176,
1276, 1317, 1447, 1577, 1598, 1658, 3060 cmꢀ1
.
Benzaldehyde (2q)22 1H NMR (300 MHz, CDCl3) 7.40–7.46 (m, 2H),
7.50–7.63 (m, 1H), 7.80–7.88 (dt, J ¼ 6.83 Hz, J ¼ 1.5 Hz, 1H), 9.96 (s, 1H)
ppm; 13C NMR (75 MHz, CDCl3) 192.39, 136.46, 134.44, 129.68,
129.02 ppm. IR (film) 650, 688, 746, 828, 1023, 1167, 1204, 1311, 1391,
1455, 1584, 1597, 1654, 1702, 2738, 2820, 2852, 3031, 3064 cmꢀ1
.
Acetophenone (2r)22 1H NMR (300 MHz, CDCl3) 2.55 (s, 3H),
7.38–7.46 (m, 2H), 7.48–7.55 (m, 1H), 7.90–7.95 (m, 2H) ppm; 13C NMR
26.53, 128.27, 128.55, 133.08, 137.05, 198.02 ppm; IR (film) 690, 760, 955,
1024, 1078, 1180, 1266, 1359, 1449, 1582, 1599, 1686, 2924, 3005, 3063 cmꢀ1
.
Octanal (2s)21 1H NMR (300 MHz, CDCl3) 0.88 (bs, 3H), 1.29 (bs,
8H), 1.62 (bs, 2H), 2.42 (t, j ¼ 8 Hz, 1H), 2.43 (t, j ¼ 8 Hz, 1H), 9.76 (t,
j ¼ 8 Hz, 1H) ppm; 13C NMR 14.0, 22.1, 22.6, 29.05, 29.15, 31.66, 43.94,
203 ppm; IR (film) 723, 947, 1078, 1379, 1429, 1465, 1728, 2714, 2857,
2928, 2956 cmꢀ1
.
Decanal (2t)21 1H NMR (300 MHz, CDCl3) 0.88 (t, j ¼ 7.6 Hz, 3H),
1.15–1.35 (bs, 14H), 1.60 (bs, 2H), 2.40 (t, j ¼ 8 Hz, 1H), 2.41 (t, j ¼ 8 Hz,
1H), 9.86 (t, j ¼ 8 Hz, 1H) ppm; 13C NMR 14.2, 22.2, 22.7, 29.3, 29.38, 29.6,
29.71, 32.0, 44.1, 203 ppm; IR (film) 718, 890, 1058, 1369, 1412, 1468, 1722,
2721, 2851, 2976 cmꢀ1
.
2-Ethylhexanal (2u)21 13C NMR 0.91 (m, 6H), 1.16–1.80 (m, 8H), 2.21
(m, 1H), 9.76 (d, j ¼ 7.4 Hz, 1H) ppm; 13C NMR 11.5, 14.1, 21.92, 22.86,
28.3, 29.31, 53.45, 206.5 ppm; IR (film) 740, 821, 910, 1020, 1080, 1140,
1268, 1321, 1452, 1722, 2720, 2860, 2925, 2954 cmꢀ1
.
ACKNOWLEDGMENTS
The authors gratefully acknowledge the Grants and Research Funding
Committee (GRFC) for financial help, National Science Foundation (ILI-IP
grant #96-50399) for partial financing the purchase of Bruker DPX-300
NMR instrument.
M. H. A. thanks Dr. Bjorn Olesen, and Dr. David Ritter for helpful
suggestions during the preparation of this manuscript.
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Springer-Verlag, New York, 1984.

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2. Ley, S.V.; Madin, A. in Comprehensive Organic Synthesis, vol. 7,
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either freshly prepared SJR or SJR that was allowed to sit in a sealed
flask for 17 weeks in the hood under ambient light.
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1
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1
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C. J.; Behnke, J. vol. II, 1993.
Received in the USA January 21, 2001

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