Triethylamine → 2-(Acryloyloxy)ethyl methacrylate

HRID 1829862Notes

Reaction equation

HRID 1829862 reaction equation
[C:1]([O:6][CH2:7][CH2:8][OH:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>ClCCl>[C:1]([O:6][CH2:7][CH2:8][O:9][C:17](=[O:20])[CH:18]=[CH2:19])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 133602-Hydroxyethyl Methacrylate

Product 1

HCID 233676582-(Acryloyloxy)ethyl methacrylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 g of hydroxyethyl methacrylate was weighed into a 250 ml r.b. flask fitted with stirrer, thermometer and nitrogen blanket. 3.88 g of triethylamine was then added followed by 80 ml of dichloromethane. The mixture was cooled and 4.15 g of acryloylchloride was added dropwise. The reaction mixture turned yellow and after 10 min a precipitate formed. Stirring was continued for 90 minutes. The precipitated material (TMEDA.HCl) was then filtered off and the organic solution extracted with sodium bicarbonate solution. The solution was then dried over anhydrous magnesium sulphate and after filtration the solvent evaporated to give a pale yellow oil (yield˜90%).

Workup

  1. customflask fitted with stirrer
  2. temperatureThe mixture was cooled
  3. customa precipitate formed
  4. waitwas continued for 90 minutes
  5. filtrationThe precipitated material (TMEDA.HCl) was then filtered off
  6. extractionthe organic solution extracted with sodium bicarbonate solution
  7. dry with materialThe solution was then dried over anhydrous magnesium sulphate
  8. filtrationafter filtration the solvent
  9. customevaporated

Sources & evidence

ORD record
ord-a9722705dcd54a4ca0862989284ed2a1
Source dataset
uspto-grants-2006_06
Patent number
US07064174B2

Reaction notes

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