Asian Journal of Chemistry; Vol. 25, No. 5 (2013), 2927-2928
NOTE
Oxidation of Alcohols to Aldehydes and Ketones by HIO
3
in Presence of NaHSO ·H O
4
2
1
2
3,*
4
MOHSEN KHADEMIAN , MARYAM KHADEMIAN , MOSTAFA RAHIMNEJAD and NADER MOKHTARIAN
1
Faculty of Chemical Engineering, Noshirvani University, Babol, Iran
Faculty of Chemistry, University of Guilan, Rasht, Iran
2
3
4
Biotechnology Research Lab., Faculty of Chemical Engineering, Noshirvani University, Babol, Iran
Islamic Azad Universtiy, Shahraza Branch, Isfhan, Iran
*
Corresponding author: E-mail: rahimnejad@nit.ac.ir; rahimnejad_mostafa@yahoo.com
(
Received: 20 January 2012; Accepted: 30 November 2012)
AJC-12483
3 4 2
Different types of alcohols are efficiently converted to their corresponding aldehyds and ketones with HIO in presence of NaHSO ·H O.
All reaction was performed in CH CN medium in good to high yields.
3
Key Words: Iodic acid, Alcohols, Aldehyds.
1
1,12
Aldehydes and ketones represent an important class of
using HIO
3
in organic transformations , we have found that
·H O can be oxidized alcohols
1
products and intermediates in the fine chemical and specialities .
The mild oxidation of alcohols is an important transformation
in organic synthesis and numerous methods using a variety of
HIO in the presence of NaHSO
3
4
2
to aldehydes and ketones under mild reaction conditions. In
present study, we wish to report an efficient, simple and low
cost method for oxidation of the above mentioned substrates
2
-4
reagents and conditions have been explored . Some of this
method involves the use of expensive reagents, long reaction
times, low yields of products and tedious work-up. Therefore,
introduction of new methods and reagents for such functional
group transformation is still in demand.
to aldehydes and ketones using HIO
3 4 2
/NaHSO ·H O reagent
system in CH CN medium.All reaction were performed under
3
mild conditions in good to high yields (eqn. 1). Yields and
reaction times are shown in (Table-1).
Application of solid acids in organic transformation have
very important role because, solid acids have many advantages
such as simplicity in handling, decreased reactor and plant
corrosion problems and more environmental safe disposal.
Also wastes and by-products can be minimized or avoided by
HIO (1.5 mmol)
3
NaHSO .H O(0.25 mmol)
4
2
1
2
(1)
1
2
R R CO
R R CHOH
Wet CH CN , reflux
3
We tried to convert alcohols to their corresponding
aldehydes and ketones in good to high yields. In all cases no
other oxidation products were observed.
5
,6
developing cleaner synthesis routes among solid acid,
oxidation of alcohols with periodic acid with various catalysts
has been well documented. In recent years, periodic acid has
been employed for oxidation of alcohols with various
catalysts such as pyridinium fluorochromate, pyridinium
chlorochromate, chromium(III) acetylacetonate and Fe(III)/
To a solution of substrate (1 mmol) in CH
which is moisture with a drop of water, were added HIO
mmol, 0.264 g) and NaHSO ·H O (0.25 mmol, 0.035 g) and
3
CN (3 mL),
3
(1.5
4
2
refluxed for the appropriate time (Table-1). The progress of
the reaction was monitored by TLC. When the reaction was
complete the mixture was filtered. The solid residue was
7
,8
2
-picolinic acid .
To the best of our knowledge all of the reported above
mentioned catalysts have toxic transition metal cations or
reaction condition is harsh. Therefore, we decided to choose
safe and cheap catalyst for activation of periodic acid and iodic
acid under mild condition.
washed with CH
the residue was triturated with H
extracted with diethyl ether (3 × 5 mL) the combined organic
solution was dried over MgSO and filtered. Evaporation of
3
CN (5 mL). The solvent was evaporated and
2
O (10 mL). The product was
4
In continuation of our studies on application of metal
solvent followed by column chromatography on silica gel gave
the corresponding carbonyl compounds in good to high yields.
9,10
hydrogen sulfates in promotion of organic reaction and also