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Citation: NIAN Bao-Yi, XU Gang, WU Jian-Ping, YANG Li-Rong. Synthesis of Racemic Menthols via Catalyzed Hydrogenation of Thymol Based on Hydroxyl Protection[J]. Chinese Journal of Applied Chemistry, ;2008, 25(2): 169-172. shu

Synthesis of Racemic Menthols via Catalyzed Hydrogenation of Thymol Based on Hydroxyl Protection

NIAN Bao-Yi ^a,b,, ,
XU Gang ^b ,
WU Jian-Ping ^b ,
YANG Li-Rong ^b

1.
a Department of Chemistry & Biology Engineering, Sanming College, Sanming 365004;
2.
b College of Material Science & Chemistry Engineering, Zhejiang University, Hangzhou 310027

Corresponding author: NIAN Bao-Yi,
Received Date: 9 February 2007
Available Online: 27 May 2007
Fund Project: 国家自然科学基金(20336010) (20336010)国家"九七三"计划(2003CB716008) (2003CB716008)福建省教育厅科研基金(JA06050)资助项目 (JA06050)

The racemic mixture of menthone was synthesized by catalytic hydrogenation of thymol based on hydroxyl protection using TMS(trimethylchorosilane) with excellent selectivity and good yield(both of 100%) under mild and neutral reaction conditions.The racemic menthone was hydrogenated to racemic menthol over 8% Cu/SiO₂ in a medium with pH=4 by tartaric acid modifying.A selectivity of 72% for the desired product,(±)-menthol,was achieved under a pressure of 2 MPa,at a temperature of 150℃.For this novel process,the mechanism of reaction was proposed.Menthenol is firstly accomplished by hydrogenation of thymol with hydroxyl protection,secondly the menthenol which is unstable in air was transformed completely to the corresponding racemic menthones,and finally,racemic menthones were hydrogenated to racemic menthols.This proposed approach is promising for independent manufacture of flavors with the optical purity of(-)-menthol in the future.
- menthol,
- menthone,
- thymol of hydroxyl protection,
- menthenol,
- catalyzed hydrogenation,
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