Ethanol → 3-(4-Phenylphenoxy)-1-propanol

HRID 1377894Notes

Reaction equation

HRID 1377894 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)C.Br[CH2:18][CH2:19][CH2:20][OH:21].[OH-].[Na+]>O>[OH:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 71034-HydroxybiphenylHCID 123083-Bromo-1-propanolHCID 14798Sodium Hydroxide2×

Product 1

HCID 283517393-(4-Phenylphenoxy)-1-propanolYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 200 ml flask, 7.82 g (41.1 mmol) of 4-hydroxybiphenyl, 83 ml of ethanol, 6 g (43.2 mmol) of 3-bromo-1-propanol and a NaOH aqueous solution (1.73 g (43.2 mmol) of NaOH/6 ml of water) were sequentially added, and the mixture was heated and refluxed for 6.5 hours. To the reaction solution, 50 ml of water was added, whereupon precipitated crystals were collected by filtration and recrystallized from ethanol to obtain 4.0 g (yield: 43%) of 4-(3-hydroxypropoxy)biphenyl (1) as a colorless powder.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 6.5 hours
  3. customwhereupon precipitated crystals
  4. filtrationwere collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-aa8967bfc4a24186a632262348ff5515
Source dataset
uspto-grants-1997_09
Patent number
US05665856

Reaction notes

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