Acetic Acid → 4-(4-Methoxyphenyl)butyric acid

HRID 1817191Notes

Reaction equation

HRID 1817191 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1.C(O)(=O)C>[C].[Pd].C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 766134-Methoxy-gamma-oxobenzenebutanoic acid

Product 1

HCID 782804-(4-Methoxyphenyl)butyric acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After 4-(4-methoxyphenyl)-4-oxobutanoic acid (40 g) was added to (not completely dissolved in) a mixed solvent of acetic acid (100 ml) and THF (100 ml), 10% palladium-carbon (50%-wet) (4 g) was added thereto and the resulting mixture was stirred for 9 hours under a hydrogen atmosphere (0.4 MPa). The catalyst was removed by filtration through Celite and toluene was added to the residue. The solvent was distilled off under reduced pressure to obtain 4-(4-methoxyphenyl)butanoic acid quantitatively.

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration through Celite and toluene
  3. additionwas added to the residue
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dbcd9f3039c74d649cac5e72e6c8c056
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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