2-Chloroethanol → 1-chloro-3-(2-chloroethoxy)propan-2-ol

HRID 1729345Notes

Reaction equation

HRID 1729345 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].[CH2:5]([CH:7]1[O:9][CH2:8]1)[Cl:6]>>[Cl:1][CH2:2][CH:3]([OH:4])[CH2:8][O:9][CH2:7][CH2:5][Cl:6]

Participants

3

Procedure

A mixture consisting of 100 g 2-chloroethanol (12.4 mol), 573 g epichlorohydrin (6.2 mol) and 20 g of an acidic ion exchange resin was refluxed for 24 hours. The mixture was then filtered to remove the ion exchange resin and the excess alcohol and unreacted epichlorohydrin were removed by distillation. The residue was distilled under vacuum and the product 1-chloro-3-(2-chloroethoxy)-2-propanol (804 g, 75% yield) distilled between 89° and 91° C. at 0.05 mm Hg.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe mixture was then filtered
  3. customto remove the ion exchange resin
  4. customthe excess alcohol and unreacted epichlorohydrin were removed by distillation
  5. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-f7351e4436d745e9992822c78330fd37
Source dataset
uspto-grants-1994_07
Patent number
US05332790

Reaction notes

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