Methacrylic Acid → Glycidyl methacrylate

HRID 1007742Notes

Reaction equation

HRID 1007742 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([CH:9]1[O:11][CH2:10]1)Cl>>[C:1]([O:6][CH2:7][CH:9]1[O:11][CH2:10]1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

3

Reactant 2

HCID 4093Methacrylic AcidHCID 7835Epichlorohydrin

Product 1

HCID 7837Glycidyl methacrylateYield 73%

Procedure

Methacrylic acid (34.4 g, 0.4 mole) was dissolved in 50 g (0.63 mole) of pyridine anhydride. The exothermic reaction was cooled by placing the reaction vessel in a liquid nitrogen-isopropyl alcohol bath. Thereafter, 50.8 g (0.55 mole) of epichlorohydrin was added dropwise. The cooling bath was removed, and the reaction mixture was stirred at room temperature for over 36 hours. The reaction was monitored using TLC. The reaction mixture was transferred to a separatory funnel, neutralized using 1 N aqueous sulfuric acid solution, and extracted with dichloromethane. The organic layer was washed with deionized water, concentrated under reduced pressure, and purified by distillation under reduced pressure to provide the product (yield 73%).

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled
  3. customThe cooling bath was removed
  4. customThe reaction mixture was transferred to a separatory funnel
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with deionized water
  7. concentrationconcentrated under reduced pressure
  8. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-45d2b1ce39fa4d37a9bc4d3510acbdd1
Source dataset
uspto-grants-2004_09
Patent number
US06797451B2

Reaction notes

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