4-(cyclopent-1-en-1-yl)benzoic acid → 4-Cyclopentylbenzoic acid

HRID 1174972Notes

Reaction equation

HRID 1174972 reaction equation
[C:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>CCO.[Pd]>[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 2779144-(cyclopent-1-en-1-yl)benzoic acid

Product 1

HCID 141636714-Cyclopentylbenzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-cyclopent-1-enyl-benzoic acid (2.6 g, 13.8 mmol) in EtOH (20 mL) is hydrogenated with 10% Pd/C (0.25 g) at 20 psi H2 for 2 h. It is filtered through Celite® and concentrated to give 2.46 g (95%) of the title compound. LC/MS (m/z): calcd for C12H14O2 (M−H)−: 189.2; found: 189.2.

Workup

  1. filtrationIt is filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5f035522bb9643a6a3911283070ce61b
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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