Ethyl Acetate → 4-(4-Hydroxyphenyl)butanoic acid

HRID 1881029Notes

Reaction equation

HRID 1881029 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.C(OCC)(=O)C>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

5

Reactant 2

HCID 8857Ethyl AcetateHCID 782804-(4-Methoxyphenyl)butyric acid

Product 1

HCID 2799834-(4-Hydroxyphenyl)butanoic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

4-(4-methoxyphenyl)butanoic acid (5.0 g) was dissolved in 48% hydrobromic acid (50 mL) and acetic acid (80 mL), then the solution was refluxed by heating for 6 hours. Ethyl acetate (300 mL) is added into the reaction solution, then organic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL), dried on anhydrous sodium sulfate, filtered and vacuum concentrated, then washed with n-hexane to give the above-identified compound (4.6 g, yield 99%).

Workup

  1. temperatureby heating for 6 hours
  2. washorganic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL)
  3. dry with materialdried on anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationvacuum concentrated
  6. washwashed with n-hexane

Sources & evidence

ORD record
ord-7417d14616864849bdf02a0f2b7c8085
Source dataset
uspto-grants-2012_11
Patent number
US08318781B2

Reaction notes

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