(-)-Isopulegol → (+)-Isopulegol

HRID 2174407Notes

Reaction equation

HRID 2174407 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

After the catalyst solution obtained in Example 34-1 was cooled to from 0 to 5° C., 1.54 g (10.0 mmol, optical purity: 96.6% e.e.) of 1-citronellal ((S)-citronellal) was added dropwise. The resulting mixture was stirred overnight at from 0 to 5° C. After completion of the reaction, 2 mL of water was added to the reaction mixture. The organic layer was analyzed using gas chromatography. As a result, it was found that a substrate conversion ratio was 89.2%, an isopulegol selectivity was 88.1%, and a d-n-isopulegol:(the other isomers) ratio was 96.9:3.1.

Workup

  1. additionwas added dropwise
  2. additionwas added to the reaction mixture

Sources & evidence

ORD record
ord-79d33d735fd84177a5a8c7f08540813f
Source dataset
uspto-grants-2015_06
Patent number
US09061959B2

Reaction notes

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