Acetic Acid → 4-(3-Chlorophenyl)phenol

HRID 1600909Notes

Reaction equation

HRID 1600909 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C.Br>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 27576351,1'-Biphenyl, 3-chloro-4'-methoxy-

Product 1

HCID 144680054-(3-Chlorophenyl)phenolYield 76.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3'-chloro-4-methoxybiphenyl (2.00 g), acetic acid (25 ml) and concentrated hydrobromic acid (25 ml) was heated at reflux for 6 hours. After cooling the reaction was added to water (200 ml) and the solution extracted with ether (300 ml). The ethereal solution was washed with saturated aqueous sodium hydrogencarbonate solution (2×150 ml), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:hexane (1:1) then dichloromethane to give the sub-title compound as a white solid (1.44 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling the reaction
  4. extractionthe solution extracted with ether (300 ml)
  5. washThe ethereal solution was washed with saturated aqueous sodium hydrogencarbonate solution (2×150 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography over silica eluting with dichloromethane:hexane (1:1)

Sources & evidence

ORD record
ord-0bb43af986144a0a97621ef69959eed8
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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