4-(4-Methoxyphenyl)butyric acid → 4-(4-Hydroxyphenyl)butanoic acid

HRID 2365489Notes

Reaction equation

HRID 2365489 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:5][CH:4]=1>Br.CC(O)=O>[OH: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

4

Reactant 1

HCID 782804-(4-Methoxyphenyl)butyric acid

Product 1

HCID 2799834-(4-Hydroxyphenyl)butanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

4-(4-Methoxyphenyl)butyric acid (25 g, 129 mmol) is dissolved in 48% HBr (125 ml) and AcOH (125 ml). The resultant solution is heated at 150° C. overnight. The resultant mixture is concentrated in vacuo and the residue taken up in EtOAc (500 ml). This solution is washed with water (500 ml), dried (MgSO4) and concentrated to give 4-(4-Hydroxy-phenyl)-butyric acid as a tan solid; 1H NMR (d6-DMSO): 1.72 (2H, tt, J=7.4 and 7.8 Hz), 2.18 (2H, t, J=7.4 Hz), 2.45 (2H, t, J=7.8 Hz), 6.66 (2H, dd, J=1.98 and 9.3 Hz), 6.96 (2H, dd, J=2.8 and 9.3 Hz), 9.12 (1H, s), 12.0 (1H, s).

Workup

  1. concentrationThe resultant mixture is concentrated in vacuo
  2. washThis solution is washed with water (500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-37fd3779f4324a1da76c93870fe3198f
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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