An Efficient Oxidation of Alcohols
Letters in Organic Chemistry, 2018, Vol. 15, No. 10 897
3
.7. 4-Methoxybenzaldehyde (7a)
3.17. α-Tetralone (17a)
1
1
H NMR (300 MHz, CDCl
3
) δ 9.91 (s, 1H), 7.84(d, 2H),
3
H NMR (300 MHz, CDCl ) δ 8.02 (d, J = 7.8 Hz, 1H),
7
.01(d, 2H), 3.90(s, 3H).
7.46 (t, J = 7.5 Hz, 1H), 7.34-7.11 (m, 2H), 3.17-2.84 (m,
+
2H), 2.78-2.47 (m, 2H), 2.14 (dd, J = 12.9, 6.7 Hz, 2H).
Mass: 136(M ) C
8
H
8
O
2
.
+
Mass: 146(M ) C10
H
10O.
3
.8. Piperonal (8a)
1
3.18. Cyclohexanone (18a)
3
H NMR (300 MHz, CDCl ) δ d 9.73 (s, 1H), 7.36 (dd, J
=
8.0, 1.6 Hz, 1H), 7.25 (d, J = 1.6 Hz, 1H), 6.88 (d, J = 8.0
1H NMR (300 MHz, CDCl
3
) δ 2.34 (t, J = 6.6Hz, 4H),
Hz, 1H), 6.09 (s, 2H).
1.87 (m, 4H), 1.42-1.72 (m, 2H).
+
+
Mass: 150(M ) C
8
H
6
O
3
.
Mass:98.07(M ) C
6
H
10O.
3
.9. 4-Nitrobenzaldehyde (9a)
3.19. Octanal (19a)
1
H NMR (300 MHz, CDCl
3
) δ 10.17 (s, 1H), 8.41(d, J =
1H NMR (300 MHz, D
2
O) δ 9.767(s, 2H), 2.442-2.429
8
.6, 2H), 8.09(d, J=8.9 2H).
(d, 3H), 1.646-1.631 (m, 4H-8H), 1.321-1.307 (t, 9H).
+
+
Mass: 151(M ) C
7
H
5
NO
3
.
Mass: 128.12(M ) C
8
H
16O.
3
.10. Acetophenone (10a)
3.20. 2-Octanone (20a)
1
1
H NMR (300 MHz, CDCl
3
) δ 7.95 (d, J = 7.0 Hz, 2H),
3
H NMR (300 MHz, CDCl ) δ 2.42 (t, J = 7.5Hz, 2H),
7
.69 – 7.30 (m, 3H), 2.59 (s, 3H).
2.14 (s, 3H), 1.52-1.62 (m, 2H), 1.27-1.31 (m, 6H), 0.88 (t,
J = 7.5Hz, 3H). Mass: 128.12(M ) C H16O.
8
+
+
Mass: 156(M ) C11
H
8
O.
CONCLUSION
3
.11. Propiophenone (11a)
1
In summary, we have demonstrated that primary, secon-
dary benzylic alcohols, and aliphatic alcohols can be effec-
tively converted to their corresponding carbonyl products
with DBDMH in aqueous hydrogen peroxide. Thus, the
present method may be served as a cost-effective, general
and environmentally benign alternative to the existing meth-
ods for the oxidation of alcohols.
H NMR (300 MHz, CDCl
3
) δ 7.95 (d, J = 7.0 Hz, 2H),
7
.60 – 7.26 (m, 3H), 2.97 (q, J = 7.2 Hz, 2H), 1.21 (t, J = 7.2
Hz, 3H).
+
Mass: 134(M ) C
9
H10O.
3
.12. 1-(p-Tolyl)ethanone (12a)
1
3
H NMR (300 MHz, CDCl ) δ 7.84 (t, J = 8.6 Hz, 2H),
7
.40 – 6.88 (m, 2H), 2.57 (s, 3H), 2.40 (s, 3H).
CONSENT FOR PUBLICATION
+
Mass: 136(M ) C
9
H
10O.
Not applicable.
3
.13. (4-Chlorophenyl)ethanone (13a)
CONFLICT OF INTEREST
1
3
H NMR (300 MHz, CDCl ) δ 8.02 –7.73 (m, 2H), 7.56 –
The authors declare no conflict of interest, financial or
otherwise.
7
.27 (m, 2H), 2.58 (s, 3H).
+
Mass: 155(M ) C
8
H
7
ClO.
ACKNOWLEDGEMENTS
3
.14. (4-Bromophenyl)ethanone (14a)
This research was supported by the Chung-Ang Univer-
sity Research Scholarship Grants in 2017.
1
3
H NMR (300 MHz, CDCl ) δ 7.81 (m, 2H), 7.57 (m,
2
H), 2.57 (s, 3H).
REFERENCES
+
Mass: 197(M ) C
8
H
7
BrO.
[
1]
Fleming, I. In Comprehensive Organic Synthesis; Trost, B.M.; Ley,
S.V., Eds.; Pergamon, Oxford, 1991, Vol. 7.
3
.15. Benzophenone (15a)
[
2]
Tojo, G.; Fernández, M. (Eds.), Oxidation of Alcohols to Aldehydes
and Ketones: A Guide to Current Common Practice, Springer, Ber-
lin, 2006.
1
3
H NMR (300 MHz, CDCl ) δ 7.45-7.49 (t, J = 7.5, 4H),
7
.55-7.60 (t, J = 7.2, 2H), 7.79-7.81 (d, J = 7.5, 4H).
[
[4]
3]
Hajipoure, A.R.; Mallakpour, S.E.; Khoee, S. Synlett, 2000, 2, 740.
Hajipour, A.R.; Safaei, S.; Ruoho, A.E. Synth. Comm., 2009, 39,
+
Mass: 182(M ) C13
H
10O.
3
687.
[
[
5]
6]
Uchiyama, M.; Kimura, Y.; Ohta, A. Tetrahedron Lett., 2000, 41,
10013.
Yamaoka, H.; Moriya, N.; Ikunaka, M. Prg. Proc. Res. Dev., 2004,
8, 931.
3
.16. 9-Fluorene (16a)
1
3
H NMR (300 MHz, CDCl ) δ 7.63 (d, J = 7.4 Hz, 2H),
7
.48-7.44 (m, 4H), 7.29-7.26 (m, 2H).
[7]
8]
Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org.
Chem., 1998, 63, 1750.
Ni, J.; Yu, W-J.; He, L.; Sun, H.; Cao, Y.; He, H-Y.; Fan, K-N.
Green Chem., 2009, 11, 756.
+
Mass: 182(M ) C13
H
10O.
[