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›› 2012, Vol. 46 ›› Issue (6): 30-34.

• 研究报告 • Previous Articles     Next Articles

Synthesis of (+)-2-Hydroxy-3-Pinanone from (-)-α-Pinene by Selective Oxidation

LIU Bing1, BI Zhong-bao2, WANG Shi-fa2   

  1. 1. Nanjing University of Finance & Economics, National Engineering Lab.for Food Storage and Transportation, Nanjing 210046, China;2. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China
  • Received:2012-07-28 Revised:1900-01-01 Online:2012-11-30 Published:2012-11-30

Abstract: (+)-2-hydroxy-3-pinanone was synthesized through selective oxidation from (-)-α-pinene. The synthetic technology was studied and affecting factors such as different oxidation systems, amount of oxidant, reaction time and temperature were investigated. The results showed that the suitable synthetic technology of (+)-2-hydroxy-3-pinanone from (-)-α-pinene were as follows: 13.7 g α-pinene (93.0% purity),α-pinene/KMnO4 molar ratio 1:2, acetone and water used as the solvent at ratio of 110:12(mL:mL), reaction temperature 0~5℃ and reaction time 5 h. Under these conditions, the conversion of α-pinene was 97.1%, selectivity of oxidation was 78.4%, purity and yield of the product were 92.1% and 76.1%, respectively; specific rotation [α]D25+26°(c=0.5 mol/L, CHCl3). The structure of (+)-2-hydroxy-3-pinanone was determined by IR, GC-MS and 1HNMR, 13CNMR spectra.

Key words: (-)-α-pinene, (+)-2-hydroxy-3-pinanone, selective oxidation

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