2-Chloroethanol → 2-(2-methoxyphenoxy)ethanol

HRID 327645Notes

Reaction equation

HRID 327645 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].[OH-].[Na+].Cl[CH2:13][CH2:14][OH:15]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 460GuaiacolHCID 14798Sodium Hydroxide

Product 1

HCID 38041392-(2-methoxyphenoxy)ethanolYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 43.2 g (0.35 mole) of 2-methoxyphenol (guaiacol, Aldrich) in 200 ml of ethanol was stirred and treated with 29 ml (0.36 mole) of 50% sodium hydroxide solution. To this solution was added a solution of 28.2 g (0.35 mole) of 2-chloroethanol (Aldrich) in 50 ml of ethanol and the reaction mixture was heated at reflux for 2 hr. The solids were removed by filtration. The filtrate was evaporated under reduced pressure and the viscous residue was partitioned between 300 ml of 15% sodium hydroxide solution and 500 ml of ethyl ether. The organic layer was washed with 200 ml of 15% sodium hydroxide solution, 300 ml of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to give 24.5 g (42%) of the title compound as a lightly colored viscous oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hr
  3. customThe solids were removed by filtration
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe viscous residue was partitioned between 300 ml of 15% sodium hydroxide solution and 500 ml of ethyl ether
  6. washThe organic layer was washed with 200 ml of 15% sodium hydroxide solution, 300 ml of water
  7. dry with materialdried (magnesium sulfate)
  8. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-9af56caa44ad4d2ebabb3f3a222f4838
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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