Chloroacetic Acid → Oxydi(ethane-2,1-diyl) bis(chloroacetate)

HRID 1398258Notes

Reaction equation

HRID 1398258 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].[Cl:8][CH2:9][C:10]([OH:12])=O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:8][CH2:9][C:10]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][O:6][C:10](=[O:12])[CH2:9][Cl:8])=[O:12]

Participants

5

Reactant 2

HCID 300Chloroacetic AcidHCID 8117Diethylene Glycol

Product 1

HCID 15376062Oxydi(ethane-2,1-diyl) bis(chloroacetate)Yield 90.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In a 10-liter 4-neck round bottom flask equipped with a mechanical stirrer and Dean-Stark apparatus was added a solution of diethylene glycol (500 g), chloro acetic acid (980 g) and para-toluene sulphonic acid (25 g) in toluene (2.5 L). The solution was refluxed with stirring and azeotropic removal of water for 5 hours, and then cooled to room temperature. The toluene layer was washed with 5% sodium bicarbonate solution (3×1000 ml) and water (3 L). The toluene layer was dried over anhydrous sodium sulphate, filtered, and distilled to obtain chloro-acetic acid 2-[2-(2-chloro-acetoxy)-ethoxy]-ethyl ester (1.1 Kg) as light yellow oil. The product was characterized by 1H NMR (CDCl3) δ 3.75 (t, 2H, CH2), 4.12 (s, 2H, CH2), 4.36 (t, 2H, CH2)

Workup

  1. customIn a 10-liter 4-neck round bottom flask equipped with a mechanical stirrer
  2. temperatureThe solution was refluxed
  3. customazeotropic removal of water for 5 hours
  4. washThe toluene layer was washed with 5% sodium bicarbonate solution (3×1000 ml) and water (3 L)
  5. dry with materialThe toluene layer was dried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. distillationdistilled

Sources & evidence

ORD record
ord-f0b8cc8d907347409b1984275df00972
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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