Methacrylic Acid → Methyl 1-methacryloyloxyethyl carbonate

HRID 1488878Notes

Reaction equation

HRID 1488878 reaction equation
CC(C)([O-])C.[K+].[C:7]([OH:12])(=[O:11])[C:8]([CH3:10])=[CH2:9].[C:13](=[O:20])([O:16][CH:17](Cl)[CH3:18])[O:14][CH3:15]>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[C:13](=[O:20])([O:16][CH:17]([O:11][C:7](=[O:12])[C:8]([CH3:10])=[CH2:9])[CH3:18])[O:14][CH3:15]

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 135066411-Chloroethyl methyl carbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 19063416Methyl 1-methacryloyloxyethyl carbonateYield 72%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

Potassium tert. butoxide (3.70 g, 0.033 mol ) was added to a solution of methacrylic acid (2.84 g, 0.033 mol) in DMF (100 ml). Methyl 1-chloroethyl carbonate (4.55 g, 0.033 mol) from Example 1u(i) above was added to the resulting suspension. 18-crown-6 (0.61 g, 2.3 mmol) was then added and the reaction mixture was left with stirring at room temperature for 3 days. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was dissolved in chloroform (100 ml) and washed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography gave 4.46 g (72%) of the title product.

Workup

  1. waitthe reaction mixture was left
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform (100 ml)
  5. washwashed with saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ad475ae23d2d4b8d828d92becbe9555b
Source dataset
uspto-grants-1997_10
Patent number
US05676925

Reaction notes

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