Asymmetric Synthesis of L-menthol

doi:10.11944/j.issn.1000-0518.2015.06.140332

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 Lin^{a, *}, LI Huanyong^a, TAN Wei^a, WANG Sanyong^b, LI Chunrong^b, YANG Dingqiao^c

^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 Published:2015-06-10 Online: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

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:

WANG Lin, LI Huanyong, TAN Wei, WANG Sanyong, LI Chunrong, YANG Dingqiao. Asymmetric Synthesis of L-menthol[J]. Chinese Journal of Applied Chemistry, 2015, 32(6): 641-646.

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Asymmetric Synthesis of L-menthol

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