Diethyl Ether → 2-Ethoxyethyl methacrylate

HRID 1029353Notes

Reaction equation

HRID 1029353 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH:7]([O:9][CH2:10][CH3:11])=[CH2:8].CCOCC>ClCCl>[C:1]([O:6][CH2:8][CH2:7][O:9][CH2:10][CH3:11])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Procedure

To a solution of 20 g methacrylic acid in 50 ml dichloromethane was added 19 g ethyl vinyl ether in 30 ml dichloromethane. The mixture was stirred overnight at room temperature and poured into ether and washed with a saturated aqueous solution of sodium bicarbonate until the solution ceased effervescing. The organic layer was dried with MgO/MgSO4 and concentrated in vacuo. The residue was distilled at 25° C./0.1 torr to give 7.1 g (19% yield) of ethoxyethyl methacrylate. A mixture of 7.0 g ethoxyethyl methacrylate and 0.076 g AIBN in 7 ml MEK was heated to 60° C. for 24 hr and 7 ml MEK was added. This solution (solution E) was used for further evaluation.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate until the solution
  2. dry with materialThe organic layer was dried with MgO/MgSO4
  3. concentrationconcentrated in vacuo
  4. distillationThe residue was distilled at 25° C./0.1 torr

Sources & evidence

ORD record
ord-d9db743d53114528b831789ed1932e23
Source dataset
uspto-grants-1992_04
Patent number
US05102771

Reaction notes

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