Menthol → (-)-Menthol

HRID 2373726Notes

Reaction equation

HRID 2373726 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 72.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

50 ml of acetonitrile was added to 16.3 g of crude menthol (chemical purity of (L)-menthol: 95%; optical purity: 97.3% e.e.), and the mixture was warmed to 30° C. to dissolve. This solution was cooled to 5° C., and crystals precipitated were collected by filtration and distilled to obtain 11.8 g (yield: 72%) of purified (L)-menthol. Chemical purity: >99%; optical purity: 99.6% e.e.

Workup

  1. dissolutionto dissolve
  2. temperatureThis solution was cooled to 5° C.
  3. customcrystals precipitated
  4. filtrationwere collected by filtration
  5. distillationdistilled

Sources & evidence

ORD record
ord-0250b23b4832451bbf9094fe8d3f2bb5
Source dataset
uspto-grants-2008_12
Patent number
US07459587B2

Reaction notes

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