One-step Conversion of α-Pinene to Campholenic Aldehyde via VO(acac)2-catalyzed Oxidation

doi:10.3724/SP.J.1095.2010.00098

Chinese Journal of Applied Chemistry ›› 2010, Vol. 27 ›› Issue (11): 1272-1275.DOI: 10.3724/SP.J.1095.2010.00098

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One-step Conversion of α-Pinene to Campholenic Aldehyde via VO(acac)2-catalyzed Oxidation

XIAO Yi^1,2, HUANG Hong-Mei¹, MAO Li-Qiu^1,2, ZHOU Liang², XU Qiong^1,2, WANG Ji-Hui², YIN Du-Lin^1,2*

(1.Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education;
2.Institute of Fine Catalysis and Synthesis,Hunan Normal University,Changsha 410081)

Received:2010-02-05 Revised:2010-04-16 Published:2010-11-10 Online:2010-11-10

Abstract

Abstract:

Conversion of α-pinene to campholenic aldehyde was directly carried out with aqueous hydrogen peroxide as oxidant catalyzed by VO(acac)2. The effects of reaction conditions such as solvents, temperature, dosage of catalyst and time on this reaction were investigated. The results showed that high valent V5+ obtained from VO(acac)2 and H2O2 is a good redox-Lewis acid bi-functional catalyst for the transformation of α-pinene to campholenic aldehyde via oxidation and isomerization of 2,3-epoxy pinane intermediate. Under optimal reaction conditions of n(H2O2)∶n(α-pinene)∶n(VO(acac)2)=2.5∶1∶0.01, reaction temperature 20 ℃, using acetone as solvent, 58.7% selectivity of campholenic aldehyde was achieved at 50.2% conversion of α-pinene after 2 h reaction. Reacting for 6 h under the conditions described above, conversion of α-pinene can reach up to 73.0% and selectivity of major products campholenic aldehyde and verbenone were 47.2% and 13.2%, respectively.

Key words: VO( acac)2, α-pinene, campholenic aldehyde, hydrogen peroxide, catalytic oxidation

CLC Number:

XIAO Yi1,2, HUANG Hong-Mei1, MAO Li-Qiu1,2, ZHOU Liang2, XU Qiong1,2, WANG Ji-Hui2, YIN Du-Lin1,2*. One-step Conversion of α-Pinene to Campholenic Aldehyde via VO(acac)2-catalyzed Oxidation[J]. Chinese Journal of Applied Chemistry, 2010, 27(11): 1272-1275.

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One-step Conversion of α-Pinene to Campholenic Aldehyde via VO(acac)2-catalyzed Oxidation

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