(-)-Isopulegol → (-)-Menthol

HRID 2174409Notes

Reaction equation

HRID 2174409 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([C:9]([CH3:11])=[CH2:10])[CH2:4][CH2:3]1>[Ni]>[CH3:1][C@H:2]1[CH2:7][C@@H:6]([OH:8])[C@H:5]([CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 170833(-)-Isopulegol

Product 1

HCID 16666(-)-MentholYield 90.8%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In a 500-mL autoclave were added 100.0 g (0.65 mol) of the 1-isopulegol obtained in Example 42 and 0.4 g of Raney nickel in a nitrogen atmosphere. Hydrogenation was conducted under a hydrogen pressure of 2.5 MPa at 70° C. for 10 hours. The reaction mixture was filtered and the residue was distilled to obtain 92.3 g (0.59 mol, 90% e.e.) of 1-menthol.

Workup

  1. customat 70° C.
  2. customfor 10 hours
  3. filtrationThe reaction mixture was filtered
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b1e170b2a0db4232ba1c9a7cd47ab214
Source dataset
uspto-grants-2015_06
Patent number
US09061959B2

Reaction notes

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