Synthesis of (+)nopinone from (-)βpinene by selective oxidation

doi:10.3969/j.jssn.1000-2006.2010.02.021

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2010, Vol. 34 ›› Issue (02): 89-94.doi: 10.3969/j.jssn.1000-2006.2010.02.021

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Synthesis of (+)nopinone from (-)βpinene by selective oxidation

LIU Bing, AO Wangwei, YANG Yang, WANG Shifa*

College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Online:2010-05-14 Published:2010-05-14

Abstract

Abstract: (+)nopinone was synthesized through selective oxidation of (-)βpinene, and the oxidation behavior of βpinene under different oxidants and solvents system were examined. Effects of the molar ratios of βpinene/KMnO4 and H2SO4/KMnO4, types of solvents, reaction temperature and time on the conversion of βpinene and selectivity of (+)nopinone were investigated. The results showed that the suitable oxidation conditions of (-)βpinene into (+)nopinone were as follows: βpinene/KMnO4 molar ratio 1∶3, H2SO4/KMnO4 molar ratio 0.054∶1, acetone was used as the solvent, reaction temperature 15—25 ℃, and reaction time 5 h. The conversion of βpinene, selectivity of oxidation, yield of (+)nopinone, specific rotation and purity of obtained product were 94.15 %, 89.19 %, 83.97 %, [α]18D+33.86°(c 1.01, CHCl3), and 95.29 %, respectively. The structure of (+)nopinone was determined by IR, 1H NMR, 13C NMR and GCMS spectra.

CLC Number:

TQ351

LIU Bing, AO Wangwei, YANG Yang, WANG Shifa*. Synthesis of (+)nopinone from (-)βpinene by selective oxidation[J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2010, 34(02): 89-94.

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Synthesis of (+)nopinone from (-)βpinene by selective oxidation

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