Water → 4'-Propyl[1,1'-biphenyl]-4-ol

HRID 1406837Notes

Reaction equation

HRID 1406837 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].B(Br)(Br)Br.O>ClCCl>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 220687594-Methoxy-4′-propylbiphenyl

Product 1

HCID 136276804'-Propyl[1,1'-biphenyl]-4-olYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Then, 21.60 g of 4-(4-propylphenyl)anisole was dissolved in 45 mL of dichloromethane, and the resultant solution was cooled with ice. Then, 35.79 g of boron tribromide was added to the solution at such a rate that the inside temperature did not exceed 10° C., followed by stirring at room temperature for 1 hour. Water was added to separate the mixture into layers, and an organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine and dried by adding sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to yield 15.91 g of 4-(4-propylphenyl)phenol.

Workup

  1. customdid not exceed 10° C.
  2. customto separate the mixture into layers
  3. washan organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  4. customdried
  5. additionby adding sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a323e2b0fd784a9cabe0b16f2f690916
Source dataset
uspto-grants-2014_12
Patent number
US08916718B2

Reaction notes

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