Water → 1-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

HRID 1600939Notes

Reaction equation

HRID 1600939 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].O>Br.C(O)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 51036301-(4'-methoxy[1,1'-biphenyl]-3-yl)ethanone

Product 1

HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanoneYield 75.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 3'-acetyl-4-methoxybiphenyl (2.07 g) in hydrobromic acid (48%, 25 ml) and glacial acetic acid (25 ml) was heated at reflux under nitrogen for 1 hour. After cooling the mixture was poured into water and extracted with ether. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a crude yellow/brown solid The latter was purified by column chromatography over silica eluting with diethyl ether:hexane (2:3) to give the sub-title compound as a cream/orange solid (1.47 g).

Workup

  1. temperatureat reflux under nitrogen for 1 hour
  2. temperatureAfter cooling the mixture
  3. extractionextracted with ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a crude yellow/brown solid The latter
  9. customwas purified by column chromatography over silica eluting with diethyl ether:hexane (2:3)

Sources & evidence

ORD record
ord-6bb8ab69923c4ac981279aa35ec802b2
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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