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

HRID 1618849

Reaction equation

HRID 1618849 reaction equation
[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][CH:19]=1)[CH:14]1[O:16][CH2:15]1.[C:26]([O:31][CH2:32][CH2:33][OH:34])(=[O:30])[C:27]([CH3:29])=[CH2:28].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[CH3:15][O:16][CH2:14][CH2:13][O:17][CH2:10][CH2:9][O:8][CH2:7][CH3:12].[C:1]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]=[CH2:25])=[CH:20][CH:19]=1)[CH:14]1[O:16][CH2:15]1.[C:26]([O:31][CH2:32][CH2:33][OH:34])(=[O:30])[C:27]([CH3:29])=[CH2:28]

Participants

8

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 1028652-((4-Ethenylphenoxy)methyl)oxiraneHCID 11041138Tetrahydropyranyl methacrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 138471-Ethoxy-2-(2-methoxyethoxy)ethaneHCID 866432112-Tetrahydropyranyl methacrylate p-vinylphenyl glycidyl ether 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

A 500 ml three-necked flask was charged with 57.0 g (0.36 mol) of 2-tetrahydropyranyl methacrylate, 31.7 g (0.18 mol) of p-vinylphenyl glycidyl ether, 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 A-6 (2-tetrahydropyranyl methacrylate/p-vinylphenyl glycidyl ether/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-469d1e6d52d8497ab63599fba065b556
Source dataset
uspto-grants-2014_07
Patent number
US08771907B2

Linked notes

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