(-)-Isopulegol → (-)-Menthol

HRID 1513558Notes

Reaction equation

HRID 1513558 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(-)-Menthol

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

By adding 0.45 g of Raney nickel to 283.8 g of the thus obtained 1-isopulegol, 10 hours of hydrogenation was carried out at 70° C. under a hydrogen pressure of 2.5 MPa. By carrying out filtration and distillation of the reaction solution, 273.5 g (1.75 mol, 71.24% e.e.) of 1-menthol was obtained.

Workup

  1. customwas carried out at 70° C. under a hydrogen
  2. filtrationfiltration and distillation of the reaction solution

Sources & evidence

ORD record
ord-6a2790c2fc0f43289c1028732507553b
Source dataset
uspto-grants-2012_07
Patent number
US08217204B2

Reaction notes

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