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

HRID 259977Notes

Reaction equation

HRID 259977 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 were 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 1° C. at 0.05 mm Hg.

Workup

  1. temperaturewere 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-a6aa106d0c934e25a96ac65343b1b7b7
Source dataset
uspto-grants-1996_06
Patent number
US05523496

Reaction notes

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