(-)-Isopulegol → (-)-Menthol

HRID 2174410Notes

Reaction equation

HRID 2174410 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.[H][H]>[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

4

Reactant 2

HCID 170833(-)-IsopulegolHCID 178418361HCID 178418361, compound

Product 1

HCID 16666(-)-MentholYield 93.8%

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 44 and 0.4 g of Raney nickel in a nitrogen atmosphere. Hydrogenation was conducted at a hydrogen pressure of 2.5 MPa and 70° C. for 10 hours. The reaction mixture was filtered, followed by distillation to obtain 94.8 g (0.61 mol, 100% e.e.) of 1-menthol.

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationfollowed by distillation

Sources & evidence

ORD record
ord-398184f8f5cc4f3dbd1ea42ed5ac0174
Source dataset
uspto-grants-2015_06
Patent number
US09061959B2

Reaction notes

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