Jasmonic Acid → Cyclopentaneacetic acid, 3-oxo-2-pentyl-

HRID 925112

Reaction equation

HRID 925112 reaction equation
[CH3:1][CH2:2]/[CH:3]=[CH:4]\[CH2:5][C@H:6]1[C:10](=[O:11])[CH2:9][CH2:8][C@@H:7]1[CH2:12][C:13]([OH:15])=[O:14]>C1COCC1.[Pd]>[O:11]=[C:10]1[CH2:9][CH2:8][CH:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

4

Reactant 1

HCID 5281166Jasmonic Acid

Product 1

HCID 107126Cyclopentaneacetic acid, 3-oxo-2-pentyl-Yield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.5 g (11.9 mmol) jasmonic acid (i.e. 2-(3-oxo-2-(2-pentenyl)cyclopentyl)acetic acid) and Pd/C (0.5 g) in THF (50 mL) was hydrogenated at room temperature for 4 h. The reaction mixture was filtered and the filtrate was concentrated to give 2-(3-oxo-2-(pentanyl)cyclopentyl)acetic acid (2.5 g, 100%) as yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-77e18ef9347b4f978198555a7752cca6
Source dataset
uspto-grants-2016_03
Patent number
US09284274B2

Linked notes

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