Diethylene Glycol → 2-Propenoic acid, 2-(2-hydroxyethoxy)ethyl ester

HRID 1430359Notes

Reaction equation

HRID 1430359 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[C:15](Cl)(=[O:18])[CH:16]=[CH2:17]>C1COCC1>[C:15]([O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6])(=[O:18])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 616422-Propenoic acid, 2-(2-hydroxyethoxy)ethyl esterYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25 g (0.235 mol) of diethylene glycol was dissolved in 150 mL of THF. 18 mL of (0.13 mol) of triethyl amine was added, followed by the dropwise addition of 10.8 g (8 mL, 0.12 mol) of acryloyl chloride. The reaction temperature was kept below 30° C. The reaction was allowed to continue for 2 hours at room temperature. The precipitated triethyl amine hydrochloride was removed by filtration, 100 mg BHT was added and the solvent was removed under reduced pressure. Diethylene glycol monoacrylate was purified on a Prochrom LC80-system, using Kromasil 60A 10 μm spherical silica. Methylene chloride/ethyl acetate 60/40 was used as eluent at a flow rate of 200 mL/min. 10 mg BHT was added before evaporation of the eluent. 9.4 g of diethylene glycol monoacrylate was isolated.

Workup

  1. customwas kept below 30° C
  2. customThe precipitated triethyl amine hydrochloride was removed by filtration, 100 mg BHT
  3. additionwas added
  4. customthe solvent was removed under reduced pressure
  5. customDiethylene glycol monoacrylate was purified on a Prochrom LC80-system
  6. addition10 mg BHT was added before evaporation of the eluent

Sources & evidence

ORD record
ord-08b18767af984175a8ece14645a7b60f
Source dataset
uspto-grants-2015_01
Patent number
US08940811B2

Reaction notes

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