Selective reduction of aldehydes to alcohols by FeS-NH4Cl-CH3OH-H2O system

Full text of DOI:10.1081/SCC-120002707

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SELECTIVE REDUCTION OF ALDEHYDES TO ALCOHOLS
BY FeS-NH4Cl-CH3OH-H2O SYSTEM*
D. G. Desai a , S. S. Swami a & R. S. Nandurdikar a
a Chemistry Department , Rayat's A. S. C. College , Sadhana Campus, Hadapsar, Pune, 411
028, India
Published online: 16 Aug 2006.
To cite this article: D. G. Desai , S. S. Swami & R. S. Nandurdikar (2002) SELECTIVE REDUCTION OF ALDEHYDES TO ALCOHOLS
BY FeS-NH4Cl-CH3OH-H2O SYSTEM*, Synthetic Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 32:6, 931-933, DOI: 10.1081/SCC-120002707
To link to this article: http://dx.doi.org/10.1081/SCC-120002707
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SYNTHETIC COMMUNICATIONS, 32(6), 931–933 (2002)
SELECTIVE REDUCTION OF
ALDEHYDES TO ALCOHOLS BY
FeS-NH4Cl-CH3OH-H2O SYSTEM*
D. G. Desai,y S. S. Swami, and R. S. Nandurdikar
Chemistry Department, Rayat’s A. S. C. College,
Sadhana Campus, Hadapsar, Pune-411 028, India
The System FeS-NH4Cl-CH3OH-H2O reduces selectively Aldehydes
to corresponding alcohols in good yields.
Although a number of reagents are available in the literature1 for the
reduction of different functional groups, the development of mild, neutral
and selective reducing system still attract a great deal of attention of organic
chemists. In recent years, reagents based on iron find wide applications in
organic synthesis because of their ready availability, ease of handling and
low cost. Reduction of aldehydes to alcohols is an important reaction in
organic synthesis and in structure determination of many natural products.
The same is achieved by numerous reagents2–13 in literature.
We report here that the FeS-NH4Cl-CH3OH-H2O is an efficient
system for selective reduction of aldehydes to corresponding alcohols in
good yields (scheme).
The chemicals required for present reducing system are easily avail-
able, cheaper and non-toxic. The system is mild neutral, ecofriendly and
gives quite satisfactory yields which is useful addition to the existing systems
to convert aldehydes to the primary alcohols (table). It does not reduce
alicyclic ketones (Entries 12,13) as well as aromatic ketones (Entries 14,15).
y*Work carried out at R. B. N. B. College, Shriramputr-413 709, India.
Corresponding author.
931
Copyright & 2002 by Marcel Dekker, Inc.
www.dekker.com

932
DESAI, SWAMI, AND NANDURDIKAR
Scheme.
Table. Reduction of Aldehydes to Alcohols
Entry
1
2Anisaldehyde
3
4
5
6
7
8
Aldehyde/Ketone
Benzaldehyde
Time (h)
3.0
Yield (%)
B.P./(M.P.) (ꢀC)
203–204
78
57
74
65
80
83
74
72
78
NR
4.0
70
2
4-Benzaldehyde
3.5
6.0
4.0
4.0
3.5
4.0
4.0
15
(61)
(68)
(74–75)
171
(63)
2-Chlorobenzaldehyde
4-Chlorobenzaldehyde
Furfuraldehyde
1-Napthaldehyde
Cinnamaldehyde
4-Bromobenzaldehyde
4-(N,N-Dimethylamino)-
benzaldehyde
256–257
(77)
9
10
–
11
12Cyclopentanone
Benzylideneacetophenone
15
NR
–
15
NR
–
–
–
–
13
14
15
Cyclohexanone
Acetophenone
Benzophenone
15
15
15
NR
NR
NR
a. NR ¼ No Reaction.
b. In case of salicylaldehyde and vanillin reaction mixture became highly coloured.
The carbon–carbon double bond also was not affected (Entries 8, 11). The
following compounds were reduced in the laboratory (table). The progress
of the reaction was monitored by TLC and products were characterised by
comparison with authentic samples,14 suitable derivatisation and spectral
analysis (IR, PMR).
EXPERIMENTAL (GENERAL PROCEDURE
FOR REDUCTION)
Aldehyde/Ketone (10 mmol) was dissolved in a mixture of methanol
(30 ml) and water (10 ml). To this commercial powdered iron sulphide

SELECTIVE REDUCTION OF ALDEHYDES
933
(50 mmol) and ammonium chloride (50 mmol) were added. It was refluxed in
water bath (TLC monitoring, see table). When the reaction is over,
residue was filtered, washed with methanol (2 Â 5 ml). The solvent was
removed from combined filtrate and washings by distillation under reduced
pressure and residue was extracted with methylene chloride (3 Â 30 ml).
The combined organic layer was washed with water (3 Â 30 ml) and dried
over anhydrous sodium sulphate. Removal of solvent under reduced press-
ure furnished an alcohol which was further purified by distillation.
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Received in the Netherlands April 12, 2001