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

HRID 1613347Notes

Reaction equation

HRID 1613347 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-032c83da2ef149d9810d02450ba84ca6
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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