Acetic Acid → 4'-Fluoro-2'-methyl[1,1'-biphenyl]-4-ol

HRID 442270Notes

Reaction equation

HRID 442270 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1.C(O)(=O)C.I>O>[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24841Hydrogen iodideHCID 214164214-Fluoro-4′-methoxy-2-methyl-1,1′-biphenyl

Product 1

HCID 214164314'-Fluoro-2'-methyl[1,1'-biphenyl]-4-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.1 grams of 4-(2'-methyl-4'-fluorophenyl)-anisole in 50 ml. of boiling acetic acid is added 5 ml. of hydriodic acid and the boiling continued for 3 hours. Water is added and the reaction mixture cooled and the 4-(2'-methyl-4'-fluorophenyl)-phenol crystallizes. Further purification is then achieved by recrystallization of the solid from aqueous ethanol to yield 4-(2'-methyl-4'-fluorophenyl)-phenol.

Workup

  1. temperaturethe reaction mixture cooled
  2. customthe 4-(2'-methyl-4'-fluorophenyl)-phenol crystallizes
  3. customFurther purification
  4. customis then achieved by recrystallization of the solid from aqueous ethanol

Sources & evidence

ORD record
ord-01fb65b25f014575859985c57f6e3c3e
Source dataset
uspto-grants-1977_08
Patent number
US04044049

Reaction notes

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