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

HRID 256498

Reaction equation

HRID 256498 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+]>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.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

7

Reactant 3

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

Product 1

HCID 139591154-(8-Hydroxyoctyl)oxybiphenylYield 65.4%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 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--dioctyl-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-ef4b0c88312a4ec6908e3248d17efc7c
Source dataset
uspto-grants-1987_10
Patent number
US04703130

Linked notes

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