Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (6): 641-646.DOI: 10.11944/j.issn.1000-0518.2015.06.140332

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Asymmetric Synthesis of L-menthol

WANG Lina, *, LI Huanyonga, TAN Weia, WANG Sanyongb, LI Chunrongb, YANG Dingqiaoc   

  1. aAnalytical and Testing Center,Ji'nan University,Guangzhou 510632,China
    bGuangdong Food Industry Institute,Guangzhou 510308,China
    cSchool of Chemistry and Environment,South China Normal University,Guangzhou 510006,China
  • Received:2014-09-25 Accepted:2015-01-13 Online:2015-06-10 Published:2015-06-10
  • Contact: Lin WANG
  • Supported by:
    Supported by the Industry-Academia Cooperation Project of the Ministry of Education of Guangdong Province(No.2011A090200039), the Natural Science Foundation of Guangdong Province(No.S2013020013091)

Abstract:

L-menthol was synthesized from the starting materials of 4-hydroxy-2-butanone and mesityl oxide in four steps consisting of aldol condensation, asymmetric hydrogenation, reduction of carbonyl group, and ruthenium catalyzed hydrogenation. The total yield is 33% and the diastereomeric excess is 93%. Furthermore, the effects of copper catalysts and their loading, chiral ligands, reaction time and solvents on the asymmetric hydrogenation of piperitenone were discussed in details. The intermediates and target compound were identified and characterized by 1H NMR, 13C NMR and HRMS.

 

Key words: L-menthol, asymmetric hydrogenation, enantioselectivity, chiral ligand

CLC Number: