(-)-Isopulegol → (+)-Isopulegol

HRID 2193858Notes

Reaction equation

HRID 2193858 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>O>[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

Participants

3

Reactant 1

HCID 170833(-)-Isopulegol

Product 1

HCID 1268090(+)-Isopulegol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

The catalyst solution obtained in Example 7-1 was cooled to 0 to 5° C., and 1.54 g (10.0 mmol) of l-citronellal was added dropwise to the solution, followed by stirring at 0 to 5° C. overnight. After completion of the reaction, 2 ml of water was added to the reaction mixture, and an organic layer was analyzed with gas chromatography. As a result, substrate conversion was 89.2%, isopulegol conversion was 88.1%, and the ratio of l-n-isopulegol to the other isomers was 96.9:3.1.

Workup

  1. additionwas added to the reaction mixture

Sources & evidence

ORD record
ord-b62a33e3a8ca493084c7e035560aff2d
Source dataset
uspto-grants-2012_12
Patent number
US08329931B2

Reaction notes

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