2-Chloroethanol → 2-[4-(Methylthio)phenoxy]ethanol

HRID 330409Notes

Reaction equation

HRID 330409 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][OH:13])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 140864-(Methylthio)phenol

Product 1

HCID 148552542-[4-(Methylthio)phenoxy]ethanolYield 28.6%

Procedure

A mixture of 105.46 g (0.753 mole) of 4-(methylthio)phenol, 62.0 g (0.772 mole) of 2-chloroethanol and 105 g (0.761 mole) of potassium carbonate in approximately one liter of acetonitrite was refluxed overnight. The cooled mixture was filtered, and the solvent was removed in vacuo to give a solid. This was recrystallized from diethyl ether-hexane to give 39.59 g (28.6%) of the product as a white, crystalline solid, mp 55°-56° C.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe cooled mixture was filtered
  3. customthe solvent was removed in vacuo
  4. customto give a solid
  5. customThis was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-344112a3d6ed43fd906722386f18e2c3
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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