4-Ethenylphenyl acetate → p-Vinylphenyl glycidyl ether 1-ethoxyethyl methacrylate p-acetoxystyrene

HRID 574028

Reaction equation

HRID 574028 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH2:13])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[C:14]([O:19][CH:20]([O:22][CH2:23][CH3:24])[CH3:21])(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:25]([O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[CH2:34])=[CH:31][CH:30]=1)(=[O:27])[CH3:26].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH2:13])=[CH:8][CH:7]=1)[CH:2]1[O:4][CH2:3]1.[C:14]([O:19][CH:20]([O:22][CH2:23][CH3:24])[CH3:21])(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:25]([O:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[CH2:34])=[CH:31][CH:30]=1)(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 758214-Ethenylphenyl acetateHCID 1028652-((4-Ethenylphenoxy)methyl)oxiraneHCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)HCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 1

HCID 86655547p-Vinylphenyl glycidyl ether 1-ethoxyethyl methacrylate p-acetoxystyrene

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 52.9 g (0.30 mol) of p-vinylphenyl glycidyl ether, 19.0 g (0.12 mol) of 1-ethoxyethyl methacrylate, 29.2 g (0.18 mol) of p-acetoxystyrene 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 dimethyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A2-4 (p-vinylphenyl glycidyl ether/1-ethoxyethyl methacrylate/p-acetoxystyrene) as a diethylene glycol dimethyl 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 dimethyl ether
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-384377b14f4e418f88fb24a36393fb6f
Source dataset
uspto-grants-2015_05
Patent number
US09034440B2

Linked notes

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