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tert-Butyl methacrylate → t-Butyl methacrylate 4-vinylquinoline 4-acetoxystyrene

HRID 1668276
Notes
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Reaction equation

HRID 1668276 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:13]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[C:14]([CH3:16])=[CH2:15].[CH:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1)=[CH2:24].N(C(C)(C)C(OC)=O)=NC(C)(C)C(OC)=O>C1(=O)CCCCC1.CCCCCC>[C:13]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:17])[C:14]([CH3:16])=[CH2:15].[CH:23]([C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1)=[CH2:24].[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11448tert-Butyl methacrylateHCID 757631,1'-Dimethyl 2,2'-(1,2-diazenediyl)bis(2-methylpropanoate)HCID 758214-Ethenylphenyl acetateHCID 133195774-Ethenylquinoline

Product 1

HCID 86629094t-Butyl methacrylate 4-vinylquinoline 4-acetoxystyreneYield 299.6%

Reagents, catalysts & solvents 2

HCID 7967CyclohexanoneSolvent2×
HCID 8058HexaneSolvent

Procedure

4-Acetoxystyrene (29.19 g) (0.18 mol), 12.80 g (0.09 mol) of t-butyl methacrylate, 4.66 g (0.03 mol) of 4-vinylquinoline, and 3.45 g (0.015 mol) of polymerization initiator V-601 (manufactured by Wako Pure Chemical Industries) are dissolved in 148.99 g of cyclohexanone. Cyclohexanone (37.25 g) is put in a reaction vessel and the above solution is dropped into the reaction system at 80° C. over 6 hours under nitrogen gas atmosphere. After dropping, the reaction solution is stirred while heating for 2 hours, and then allowed to cool to room temperature. The solution is dropped into 2.5 liters of hexane to thereby precipitate and filter the polymer. The solid filtered is roughly washed with 500 ml of hexane and dried under reduced pressure to obtain 41.30 g of t-butyl methacrylate/4-vinylquinoline/4-acetoxystyrene copolymer.

Workup

  1. additionthe above solution is dropped into the reaction system at 80° C. over 6 hours under nitrogen gas atmosphere
  2. temperaturewhile heating for 2 hours
  3. customto thereby precipitate
  4. filtrationfilter the polymer
  5. filtrationThe solid filtered
  6. washis roughly washed with 500 ml of hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-ff772c5ce1d44ddb8c9cd9f6dbc6d075
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989137B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes