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

HRID 1613344Notes

Reaction equation

HRID 1613344 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 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-d87b6a85935f400596a7a04e3e61541a
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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