Methacrylic Acid → gamma-Butyrolactone methacrylate

HRID 1979024Notes

Reaction equation

HRID 1979024 reaction equation
Br[CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4].[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=[CH2:10].C(N(CC)CC)C>C(C(C)=O)C(C)C>[C:8]([O:13][CH:2]1[CH2:7][CH2:6][O:5][C:3]1=[O:4])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 954632(3H)-Furanone, 3-bromodihydro-2×

Product 1

HCID 11206014gamma-Butyrolactone methacrylateYield 85%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

100 g of α-bromo-γ-butyrolactone and 104.4 g of methacrylic acid (2.0 mole times with respect to α-bromo-γ-butyrolactone) were charged, and methyl isobutyl ketone was added thereto in an amount of 3 weight times that of α-bromo-γ-butyrolactone to prepare a solution. Then, 183.6 g of triethylamine (3.0 mole times with respect to α-bromo-γ-butyrolactone) was added dropwise thereto, followed by stirring at room temperature for about 10 hours. After filtration, an organic layer was washed with 5% by weight aqueous solution of sodium bicarbonate, followed by washing with water for 2 times. The organic layer was concentrated to obtain α-methacryloyloxy-γ-butyrolactone represented by the following formula in a 85% yield.

Workup

  1. filtrationAfter filtration
  2. washan organic layer was washed with 5% by weight aqueous solution of sodium bicarbonate
  3. washby washing with water for 2 times
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-5b8e4dd6c58e47f68aa2394d46d03b36
Source dataset
uspto-grants-2001_05
Patent number
US06239231B1

Reaction notes

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