Perchloric Acid → Benzenebutanoic acid, 4-cyclohexyl-

HRID 861865Notes

Reaction equation

HRID 861865 reaction equation
[CH:1]1([C:7]2[CH:19]=[CH:18][C:10]([C:11]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl(O)(=O)(=O)=O>[C].[Pd].C(O)(=O)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:18][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 1618624-(4-Cyclohexylphenyl)-4-oxobutanoic acid

Product 1

HCID 3041568Benzenebutanoic acid, 4-cyclohexyl-Yield 102.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-cyclohexylbenzoyl)propionic acid (10.7 g), acetic acid (100 ml) and perchloric acid (2.3 ml) was hydrogenated in the presence of 5% palladium carbon (50% wet, 3.0g) at room temperature under ordinary pressure. After removal of the catalyst by filtration, the filtrate was concentrated under reduced pressure. After water (100 ml) was added, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried (MgSO4), after which the solvent was evaporated off, to yield 4-(4-cyclohexylphenyl)butyric acid (10.4 g, 100%) as an oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionAfter water (100 ml) was added
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customafter which the solvent was evaporated off

Sources & evidence

ORD record
ord-8ad57db0acd24620ae9ed08cdc327bd0
Source dataset
uspto-grants-1998_02
Patent number
US05716944

Reaction notes

Loading…