2-Chloroethanol → 2-(3-Chlorophenoxy)ethanol

HRID 327631Notes

Reaction equation

HRID 327631 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:10][CH2:11][OH:12].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 79333-ChlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 802702-(3-Chlorophenoxy)ethanolYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 51.4 g (0.4 mole) of 3-chlorophenol (Aldrich Chem. Co.), 34.7 g (0.43 mole) of 2-chloroethanol (Aldrich) and 16.1 g (0.4 mole) of sodium hydroxide pellets in 500 ml of 95% ethanol was stirred and heated at reflux for 16 hr. The mixture was filtered and the filtrate was evaporated under reduced pressure to yield a semisolid residue. The residue was partitioned between methylene chloride and a 15% sodium hydroxide solution (300 ml of each). The organic layer was washed with two 300 ml portions of water, dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give 34.2 g (50%) of the title compound as a viscous oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hr
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under reduced pressure
  5. customto yield a semisolid residue
  6. customThe residue was partitioned between methylene chloride
  7. washThe organic layer was washed with two 300 ml portions of water
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-61db735dcdd943b0b7deee69d5956c9d
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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