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

HRID 343636Notes

Reaction equation

HRID 343636 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-9e0ab87c47fd417cb1c3eb6c78e3154c
Source dataset
uspto-grants-1999_01
Patent number
US05861534

Reaction notes

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