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

HRID 1425626

Reaction equation

HRID 1425626 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:44](C)(CC)[C:45]([O-:47])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[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].[CH3:15][O:16][CH2:14][CH2:13][O:17][CH2:18][CH2:19][O:47][CH2:45][CH3:44]

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

Into a 500 ml-volume three-neck flask, 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 were charged. A catalytic amount of 2,2′-azobis(methyl 2-methylpropionate) was added thereto as a radical polymerization initiator, and polymerization was allowed to proceed at 80° C. for 6 hours in a nitrogen stream. The reaction solution was cooled and then poured in a large amount of heptane to precipitate a polymer. The crystal was collected by filtration and dissolved in diethylene glycol ethyl methyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A-6 (2-tetrahydropyranyl methacrylate/p-vinylphenyl glycidyl ether/2-hydroxyethyl methacrylate) as a diethylene glycol ethyl methyl ether solution.

Workup

  1. customas a radical polymerization initiator, and polymerization
  2. temperatureThe reaction solution was cooled
  3. customto precipitate a polymer
  4. filtrationThe crystal was collected by filtration
  5. dissolutiondissolved in diethylene glycol ethyl methyl ether
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1cf600eea8b24d5da9ea525fb26e7e72
Source dataset
uspto-grants-2015_01
Patent number
US08932800B2

Linked notes

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