6556
D. Chakraborty et al. / Tetrahedron Letters 50 (2009) 6553–6556
Supplementary data
-4.8
-5.0
-5.2
-5.4
-5.6
-5.8
-6.0
-6.2
-6.4
Y = -4.236 + 2.05401 X
Supplementary data associated with this article can be found, in
References and notes
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-1.2
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-0.9
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log10
Figure 2. Van’t Hoff differential plot for the oxidation of 3,4-dichlorobenzaldehyde
with 10 mol % AgNO3 and 5 equiv of 30% H2O2 in MeCN at 50 °C.
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cyclohexanecarboxaldehyde
and
4-
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3. Conclusions
In summary, we have developed a simple, efficient, chemoselec-
tive and inexpensive catalytic method for the oxidation of alde-
hydes to carboxylic acids using a table top reagent such as
AgNO3.15 It is noteworthy that this methodology does not rely
upon ligands and other additives.
15. Typical experimental procedure: To
a stirred solution of AgNO3 (16.99 mg,
0.1 mmol) and aldehyde (1 mmol) in 2 mL MeCN was added 30% H2O2
(0.57 mL, 5 mmol). The reaction mixture was slowly heated to 50 °C. The
progress of the reaction was monitored using TLC until all aldehyde was found
consumed. The reaction was quenched with cold 10% Na2S2O3 solution and
extracted with dichloromethane. All the volatiles were removed to yield the
crude product. The crude product was treated with saturated NaHCO3 solution.
This was extracted with dichloromethane. Finally, the aqueous layer was
acidified using 2 N HCl and extracted with dichloromethane. The organic layer
was concentrated and subjected to column chromatography. Comparable
yields and purity of the products were obtained employing ethyl acetate as an
alternative solvent for work-up. The spectral data of the various carboxylic
acids were found to be satisfactory in accord with the literature.
Acknowledgements
This work was supported by Department of Science and Tech-
nology and Council of Scientific and Industrial Research, New
Delhi. The services from the NMR facility purchased under the FIST
programme, sponsored by the Department of Science and Technol-
ogy, New Delhi is gratefully acknowledged. The authors thank the
reviewers for their useful comments and suggestions.