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Frontiers of Chemistry in China

ISSN 1673-3495

ISSN 1673-3614(Online)

CN 11-5726/O6

Front Chem Chin    2009, Vol. 4 Issue (1) : 58-62    https://doi.org/10.1007/s11458-009-0002-2
RESEARCH ARTICLE
Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation
Jitai LI(), Xiaoliang LI, Xianfeng LIU, Jiejie MA
Key Laboratory of Analytical Science and Technology of Hebei Province,College of Chemistry and Environmental Science,Hebei University,Baoding 071002,China
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Abstract

The reactions of oximes with benzyl bromide catalyzed by benzyldimethyltetradecylammonium chloride are carried out at room temperature for 30-60 min in aqueous sodium hydroxide solution under ultrasound irradiation to offer O-benzyl oxime derivatives in 60-96% yields. In comparison to classical methods, the advantages of the present procedure include short reaction time, high yields and environmental friendliness.

Keywords oxime ether      phase transfer catalysis      ultrasound      etherification     
Corresponding Author(s): LI Jitai,Email:lijitai@hbu.cn   
Issue Date: 05 March 2009
 Cite this article:   
Jitai LI,Xianfeng LIU,Jiejie MA, et al. Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation[J]. Front Chem Chin, 2009, 4(1): 58-62.
 URL:  
https://academic.hep.com.cn/fcc/EN/10.1007/s11458-009-0002-2
https://academic.hep.com.cn/fcc/EN/Y2009/V4/I1/58
Fig.1  Synthesis of O-benzyl oximes
EntryCat. aSolventOxime/PhCH2Br bT/minYield/%
1NaOMeEtOH1∶1.13076
2NaOMeEtOH1∶1.110067
3NaOMeEtOH1∶1.53080
4NaOH/AEtOH1∶1.53084
5NaOH/BEtOH1∶1.53075
6NaOH/CEtOH1∶1.53089
7NaOH/CH2O1∶1.53094
Tab.1  The effect of reaction conditions on the etherification of 2-methoxybenzaldoxime with benzyl bromide under ultrasound action
EntryR1R2T/minProductIsolated yield/%
a2-CH3OC6H4H303a94
2-CH3OC6H4H30a3a67
b4-CH3OC6H4H353b86
c4-O2NC6H4H303c78
d2,4-Cl2C6H3H303d96
e2-ClC6H4H203e68
f3-ClC6H4H503f89
g4-ClC6H4H203g73
hC6H5H303h78
i4-ClC6H4CH3603i90
j4-CH3OC6H4CH3603j60
Tab.2  The reaction of oximes with benzyl bromide in aqueous media catalyzed by benzyldimethyltetradecylammoniumchloride in combination with ultrasound irradiation
Fig.2  synthesis of O-benzyl oximes
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