Potassium methacrylate → 1-Methacryloyloxyethyl 2-methacryloyloxyethyl carbonate

HRID 1938119Notes

Reaction equation

HRID 1938119 reaction equation
[C:1](=[O:15])([O:6][CH2:7][CH2:8][O:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])[O:2][CH:3](Cl)[CH3:4].[C:16]([O-:21])(=[O:20])[C:17]([CH3:19])=[CH2:18].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:1](=[O:15])([O:6][CH2:7][CH2:8][O:9][C:10](=[O:14])[C:11]([CH3:13])=[CH2:12])[O:2][CH:3]([O:21][C:16](=[O:20])[C:17]([CH3:19])=[CH2:18])[CH3:4]

Participants

5

Reactant 2

HCID 23667354Potassium methacrylateHCID 544861711-Chloroethyl 2-methacryloyloxyethyl carbonate

Product 1

HCID 537448621-Methacryloyloxyethyl 2-methacryloyloxyethyl carbonateYield 77%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Procedure

1-Chloroethyl 2-methacryloyloxyethyl carbonate (1.183 g, 5.00 mmol) is added to a suspension of freeze dried potassium methacrylate (0.683 g, 5.50 mmol) and 18-crown-6 (0.066 g, 0.25 mmol) in dimethylformamide (50 ml) under a dry N2 atmosphere. After 5 days at 20° C. the solvent is removed under reduced pressure and the residue dissolved by adding dichloromethane (60 ml) and water (30 ml). After separating the phases the aqueous layer is extracted with dichloromethane (3×30 ml) and the combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml). The organic phase is dried (MgSO4) and the solvent removed under reduced pressure to give 1.10 g (77%) of the title product. 1H NMR (60 MHz, CDCl3): δ1.63 (3H, d, J=5 Hz, CH3 --CH), 1.98 (6H, s, 2×CH3), 4.42 (4H, s, O--CH2 --CH2 --O), 5.62 (2H, m, CH=), 6.15 (2H, m, CH=), 6.84 (1H, k, J=5 Hz, CH--CH3).

Workup

  1. customAfter 5 days at 20° C. the solvent is removed under reduced pressure
  2. dissolutionthe residue dissolved
  3. additionby adding dichloromethane (60 ml) and water (30 ml)
  4. customAfter separating the phases the aqueous layer
  5. extractionis extracted with dichloromethane (3×30 ml)
  6. washthe combined organic phase washed with saturated aqueous sodium hydrogen carbonate (50 ml)
  7. dry with materialThe organic phase is dried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-aaa193db232442589c07c5a2cd102e78
Source dataset
uspto-grants-1997_12
Patent number
US05693321

Reaction notes

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