Ethylene Glycol → Ethylene bis(chloroacetate)

HRID 1038293Notes

Reaction equation

HRID 1038293 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[Cl:5][CH2:6][C:7]([OH:9])=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:5][CH2:6][C:7]([O:3][CH2:2][CH2:1][O:4][C:7](=[O:9])[CH2:6][Cl:5])=[O:9]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 300Chloroacetic Acid

Product 1

HCID 81365Ethylene bis(chloroacetate)Yield 69.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer, a solution of ethylene glycol (100 grams, 1.611 moles), chloroacetic acid (385 grams, 4.031 moles) and para toluenesulphonic acid (1 gram) in toluene (750 ml), was refluxed for 8 hours using a Dean-Stark apparatus. It was then cooled to room temperature. The toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml), dried over sodium sulfate, and distilled to provide crude 1, which was purified by high vacuum distillation to provide pure 1 (242 grams, 69.8%), which slowly crystallized to white crystals. m.p: 44° C., IH NMR (CDCl3) δ4.16 (s, 2H, CH2), 4.85 (s, 2H, CH2)

Workup

  1. customIn a 2 liter, 4 necked round bottom flask equipped with a mechanical stirrer
  2. washThe toluene layer was washed with water (2×300 ml), 5% sodium bicarbonate solution (3×500 ml) and again with water (2×300 ml)
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled
  5. customto provide crude 1, which
  6. distillationwas purified by high vacuum distillation

Sources & evidence

ORD record
ord-41facf0677bc4833b0d48110c8d4747d
Source dataset
uspto-grants-2013_10
Patent number
US08551519B2

Reaction notes

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