2-Chloroethanol → 2-(4-Methoxyphenoxy)ethanol

HRID 327626Notes

Reaction equation

HRID 327626 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][OH:13].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 90154-MethoxyphenolHCID 14798Sodium Hydroxide

Product 1

HCID 2200792-(4-Methoxyphenoxy)ethanolYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 148.8 g (1.20 mole) of p-methoxyphenol, 170.0 g (2.11 mole) of 2-chloroethanol and 47.2 g (1.18 mole) of sodium hydroxide in 1.5 liter of absolute ethanol was heated at reflux for 22 hr. The solution was filtered, and the solvent was removed from the filtrate in vacuo. The residue was crystallized from methylene chloride-hexane to give 71.4 g (35%) of title compound as a white crystalline solid, mp 69°-71° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hr
  3. filtrationThe solution was filtered
  4. customthe solvent was removed from the filtrate in vacuo
  5. customThe residue was crystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-77006c225e1d43bcbc8a1de1f001a50a
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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