4-Hydroxybiphenyl → 4-(8-Hydroxyoctyl)oxybiphenyl

HRID 2165058Notes

Reaction equation

HRID 2165058 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[C:11]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+]>O.O1CCCC1>[C:17]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:18]=[CH:19][C:20]([O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 14798Sodium HydroxideHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 139591154-(8-Hydroxyoctyl)oxybiphenylYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 37.8 g of 8-bromo-1-octanol, 30.77 g of 4-phenylphenol, 8.31 g of sodium hydroxide and 34 g of N-methyl-N,N-diocyl-1-octanaminium chloride in 100 ml of water and 175 ml of tetrahydrofuran was refluxed for 17 hours. The tetrahydrofuran was removed and the residue extracted with warm chloroform. The chloroform extract was washed with water, dried and the solvent removed. The residue was recrystallized from methanol, giving 35.26 g of the desired compound as a white solid, mp 101°-103° C.

Workup

  1. temperaturewas refluxed for 17 hours
  2. customThe tetrahydrofuran was removed
  3. extractionthe residue extracted with warm chloroform
  4. extractionThe chloroform extract
  5. washwas washed with water
  6. customdried
  7. customthe solvent removed
  8. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-ff1b4990cff641f7b1347ef005757be0
Source dataset
uspto-grants-1990_07
Patent number
US04939127

Reaction notes

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