Menthol → (-)-Menthol

HRID 2373727Notes

Reaction equation

HRID 2373727 reaction equation
[CH:1]1([CH3:11])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([OH:10])[CH2:2]1>C(#N)C>[CH3:11][C@H:1]1[CH2:2][C@@H:3]([OH:10])[C@H:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 1254Menthol

Product 1

HCID 16666(-)-MentholYield 59.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

54 g of crude menthol (content of (L)-menthol: 95.7%; optical purity: 97% e.e.; content of isomer of isomenthol: 2.5%; content of isomer of neoisomenthol: 1.8%; content of isomer of neomenthol: trace) was dissolved in 150 ml of acetonitrile at 30° C., and this solution was cooled to 5° C., followed by filtration to obtain 32 g of purified (L)-menthol. GC (gas chromatography) analysis revealed that no isomers (isomenthol, neoisomenthol, and neomenthol) were detected with the purified (L)-menthol.

Workup

  1. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-6982d7fcbdbd4a47bdd1f98b473bf6d1
Source dataset
uspto-grants-2008_12
Patent number
US07459587B2

Reaction notes

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