Benzyl methacrylate → 1-Ethoxyethyl methacrylate (1-ethyl-3-oxacyclobutyl)methyl methacrylate benzyl methacrylate

HRID 1425628Notes

Reaction equation

HRID 1425628 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([CH2:23][CH3:24])[CH2:22][O:21][CH2:20]1)(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:25]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[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>[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([CH2:23][CH3:24])[CH2:20][O:21][CH2:22]1)(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:25]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)(=[O:29])[C:26]([CH3:28])=[CH2:27]

Participants

7

Reactant 4

HCID 17236Benzyl methacrylateHCID 11159706(3-Ethyloxetan-3-yl)methyl 2-methylprop-2-enoateHCID 201933451-Ethoxyethyl Methacrylate (stabilized with MEHQ)HCID 219175032,2'-Azobis(methyl 2-methylpropanate)

Product 1

HCID 866432131-Ethoxyethyl methacrylate (1-ethyl-3-oxacyclobutyl)methyl methacrylate benzyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 47.5 g (0.3 mol) of 1-ethoxyethyl methacrylate, 33.2 g (0.18 mol) of (1-ethyl-3-oxacyclobutyl)methyl methacrylate, 21.2 g (0.12 mol) of benzyl 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 dimethyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A-8 (1-ethoxyethyl methacrylate/(1-ethyl-3-oxacyclobutyl)methyl methacrylate/benzyl methacrylate) 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-ba4619f136d54d39a7f9ce801a19c2df
Source dataset
uspto-grants-2015_01
Patent number
US08932800B2

Reaction notes

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