Hydrogen Bromide → 4-(4-Hydroxyphenyl)butanoic acid

HRID 885709Notes

Reaction equation

HRID 885709 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>C(O)(=O)C>[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 2

HCID 260Hydrogen BromideHCID 782804-(4-Methoxyphenyl)butyric acid

Product 1

HCID 2799834-(4-Hydroxyphenyl)butanoic acidYield 92.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(4-Methoxyphenyl)butanoic acid (0.97 g, 5 mmol) was mixed with HBr (50 mL) and acetic acid galacial (80 mL). The mixture was refluxed for 12 h (monitored by TLC), poured into ice, stirred for 1 h, and then extracted with DCM. The solvent was evaporated in vacuo to give the title compound (0.83 g, 92%). NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.72 (m, 2H, CH2), 2.16 (t, 2H, CH2, J=7.4 Hz), 2.45 (t, 2H, CH2, J=7.6 Hz), 6.65 (d, 2H, Ar—H, J=8.3 Hz), 6.95 (d, 2H, Ar—H, J=8.3 Hz).

Workup

  1. temperatureThe mixture was refluxed for 12 h (monitored by TLC)
  2. additionpoured into ice
  3. extractionextracted with DCM
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-44c70766d9c74d9ab3243a5c10166c3a
Source dataset
uspto-grants-2012_08
Patent number
US08242282B2

Reaction notes

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