Glycidyl acrylate → 1-Ethoxy-2-(2-methoxyethoxy)ethane

HRID 1425623Notes

Reaction equation

HRID 1425623 reaction equation
[C:1]([O:6][CH:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:17]([O:21][CH2:22][CH:23]1[O:25][CH2:24]1)(=[O:20])[CH:18]=[CH2:19].[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]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:17]([O:21][CH2:22][CH:23]1[O:25][CH2:24]1)(=[O:20])[CH:18]=[CH2:19].[C:26]([O:31][CH2:32][CH2:33][OH:34])(=[O:30])[C:27]([CH3:29])=[CH2:28].[CH3:24][O:25][CH2:23][CH2:22][O:21][CH2:17][CH2:18][O:47][CH2:45][CH3:44]

Participants

8

Reactant 4

HCID 7836Glycidyl acrylateHCID 133602-Hydroxyethyl MethacrylateHCID 218349871-Benzyloxyethyl methacrylateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 2

HCID 138471-Ethoxy-2-(2-methoxyethoxy)ethaneHCID 866432081-Benzyloxyethyl methacrylate glycidyl acrylate 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 79.3 g (0.36 mol) of 1-benzyloxyethyl methacrylate, 23.1 g (0.18 mol) of glycidyl acrylate, 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-3 (1-benzyloxyethyl methacrylate/glycidyl acrylate/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-b3787d17c7bc48b2a47dcf60f33a256d
Source dataset
uspto-grants-2015_01
Patent number
US08932800B2

Reaction notes

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