Epichlorohydrin → 3-Chloro-2-hydroxypropyl acetate

HRID 2412453Notes

Reaction equation

HRID 2412453 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)[Cl:2].[C:6]([O-:9])(=[O:8])[CH3:7].[Na+]>C(O)(=O)C>[C:6]([O:9][CH2:4][CH:3]([OH:5])[CH2:1][Cl:2])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 517045Sodium Acetate

Product 1

HCID 980693-Chloro-2-hydroxypropyl acetateYield 131.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of epichlorhydrin (27.8 g) and sodium acetate (12.3 g) in acetic acid (36 g) is heated at 50°-55° C. for 8 hours. The reaction mixture is allowed to stand overnight and concentrated in vacuum. The residue is neutralized with aqueous sodium hydrogencarbonate and shaken with ether. The ethereal layer is dried over anhydrous sodium sulfate and concentrated in vacuum. The residue is distilled in vacuum to give 1-acetoxy-3-chloro-2-propanol (30 g) as an oil boiling at 115°-116° C./13 mm Hg. The yield is 65.4%.

Workup

  1. temperatureis heated at 50°-55° C. for 8 hours
  2. concentrationconcentrated in vacuum
  3. dry with materialThe ethereal layer is dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuum
  5. distillationThe residue is distilled in vacuum

Sources & evidence

ORD record
ord-328568cbe63b4d13ba8456f8ed5d728e
Source dataset
uspto-grants-1985_01
Patent number
US04492794

Reaction notes

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