2-Chloroethanol → 2-[4-(3,5-Difluorophenoxy)phenoxy]ethanol

HRID 579951Notes

Reaction equation

HRID 579951 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[O-:17][CH2:18][CH3:19].[Na+].[Na].ClCCO>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([F:16])[CH:15]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:19][CH2:18][OH:17])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 133918364-(3,5-Difluorophenoxy)phenol

Product 1

HCID 134559112-[4-(3,5-Difluorophenoxy)phenoxy]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(3,5-Difluorophenoxy)phenol (9.0 g, 40.5 mmol) was added to an ethanolic solution of sodium ethoxide prepared from ethanol (40 ml) and sodium (939 mg, 40.9 mmol). To the resultant solution, 2-chloroethanol (3.26 g, 40.5 mmol) was dropwise added with stirring under reflux. After completion of the addition, the resultant mixture was stirred under reflux for 4 hours. After allowed to cool, ethanol was removed, and the residual oil was dissolved in toluene. The toluene layer was washed with water once, a 20% aqueous potassium hydroxide solution two times and a saturated aqueous sodium chloride solution once in order and dried over anhydrous magnesium sulfate. Removal of the solvent gave 2-[4-(3,5-difluorophenoxy)phenoxy]ethanol (6.50 g).

Workup

  1. temperatureunder reflux
  2. additionAfter completion of the addition
  3. temperatureunder reflux for 4 hours
  4. temperatureto cool
  5. customethanol was removed
  6. dissolutionthe residual oil was dissolved in toluene
  7. washThe toluene layer was washed with water once
  8. dry with materiala 20% aqueous potassium hydroxide solution two times and a saturated aqueous sodium chloride solution once in order and dried over anhydrous magnesium sulfate
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-faebbf73b80b4f00b93975f18e90ff82
Source dataset
uspto-grants-1988_06
Patent number
US04751225

Reaction notes

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