Piperitenone → (+)-Pulegone

HRID 2035387Notes

Reaction equation

HRID 2035387 reaction equation
[CH3:1][C:2]1[CH2:11][CH2:10][C:6](=[C:7]([CH3:9])[CH3:8])[C:4](=[O:5])[CH:3]=1.[H][H]>C(OCC)(=O)C>[CH3:1][C@H:2]1[CH2:3][C:4](=[O:5])[C:6](=[C:7]([CH3:8])[CH3:9])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 381152PiperitenoneHCID 178418361HCID 178418361, compound

Product 1

HCID 442495(+)-PulegoneYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 500 ml capacity autoclave was charged with 150 g (1 mol) of piperitenone, 18.6 mg (0.04 mmol) of [Rh(cod)2]PF6, 47.2 mg (0.04 mmol) of (S)-DIBM-SEGPHOS, 14.8 mg (0.02 mmol) of BrPPh3(CH2)4PPh3Br and 7.5 ml of ethyl acetate, and the reaction was carried out at 50° C. for 20 hours under a hydrogen pressure of 3 MPa. After completion of the reaction, hydrogen was purged, and the reaction solution was concentrated and distilled under a reduced pressure to obtain 136.8 g of d-pulegone (yield 90%).

Workup

  1. customwas purged
  2. concentrationthe reaction solution was concentrated
  3. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-cb3b467755b842f9942d74152d4d2989
Source dataset
uspto-grants-2013_11
Patent number
US08575086B2

Reaction notes

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