2-Hydroxyethyl Methacrylate → 1-Ethoxy-2-(2-methoxyethoxy)ethane

HRID 1618833

Reaction equation

HRID 1618833 reaction equation
[C:1]([O:6][CH:7]([O:9][CH2:10][CH3:11])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:25]([O:30][CH2:31][CH2:32][OH:33])(=[O:29])[C:26]([CH3:28])=[CH2:27].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[CH3:25][O:30][CH2:31][CH2:32][O:33][CH2:11][CH2:10][O:9][CH2:7][CH3:8].[C:1]([O:6][CH:7]([O:9][CH2:10][CH3:11])[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:25]([O:30][CH2:31][CH2:32][OH:33])(=[O:29])[C:26]([CH3:28])=[CH2:27]

Participants

8

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 17236Benzyl methacrylateHCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)HCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 138471-Ethoxy-2-(2-methoxyethoxy)ethaneHCID 673222671-Ethoxyethyl methacrylate benzyl methacrylate 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

A 500 ml three-necked flask was charged with 66.4 g (0.42 mol) of 1-ethoxyethyl methacrylate, 21.1 g (0.12 mol) of benzyl methacrylate, 7.8 g (0.06 mol) of 2-hydroxyethyl methacrylate and 300 ml of methyl isobutyl ketone. A catalytic amount of 2,2′-azobis(methyl 2-methylpropionate) as a radical polymerization initiator was added to the mixture, and polymerization was performed in a nitrogen stream at 80° C. for six hours. The obtained reaction liquid was cooled, and poured in a large volume of heptane, thereby precipitating a polymer. The polymer crystal was collected by filtration, and dissolved in diethylene glycol ethyl methyl ether. The heptane and methyl isobutyl ketone contained in the solution were distilled off in vacuum, thereby obtaining a diethylene glycol ethyl methyl ether solution of polymer A1-3 (1-ethoxyethyl methacrylate/benzyl methacrylate/2-hydroxyethyl methacrylate).

Workup

  1. customThe obtained reaction liquid
  2. temperaturewas cooled
  3. customprecipitating a polymer
  4. filtrationThe polymer crystal was collected by filtration
  5. dissolutiondissolved in diethylene glycol ethyl methyl ether
  6. distillationwere distilled off in vacuum

Sources & evidence

ORD record
ord-146aa9eb645a4b5894395c6f09eb21ce
Source dataset
uspto-grants-2014_07
Patent number
US08771907B2

Linked notes

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