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Butyl Methacrylate → Butyl Methacrylate

HRID 327270
Notes
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Reaction equation

HRID 327270 reaction equation
CN(C)CC[O:5][C:6]([O:10][Si](C)(C)C)=[C:7]([CH3:9])C.[CH2:16]([N+](CCCC)(CCCC)CCCC)CCC.C(OCCN(C)C)(=O)C(C)=C.[C:44]([O:49][CH2:50][CH2:51][CH2:52][CH3:53])(=[O:48])[C:45]([CH3:47])=[CH2:46].C(O[Si](C)(C)C)(=O)C(C)=C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(=O)OC(C)CO1.C1COCC1>[C:44]([O:49][CH2:50][CH2:51][CH2:52][CH3:53])(=[O:48])[C:45]([CH3:47])=[CH2:46].[CH3:16]/[CH:9]=[CH:7]/[C:6]([OH:5])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 7354Butyl MethacrylateHCID 16028Tetrabutylammonium2×HCID 17869(Dimethylamino)ethyl methacrylateHCID 27338392-Propenoic acid, 2-methyl-, trimethylsilyl esterHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 197346981-(2-Dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene

Product 2

HCID 7354Butyl MethacrylateHCID 637090Crotonic Acid

Reagents, catalysts & solvents 2

HCID 7924Propylene CarbonateSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.55 g (6.31 mL, 24 mmol) of 1-(2-dimethylaminoethoxy)-1-trimethylsiloxy-2-methyl-1-propene and 0.1 mL of tetrabutylammonium biacetate (0.04M in propylene carbonate) in 30 mL of THF was added a mixture of 7.6 g (8.1 mL, 48 mmol) of 2-dimethylaminoethyl methacrylate (purified by passage over a column of basic alumina under argon), and 23.9 g (26.7 mL, 168 mmol) of n-butyl methacrylate (purified by passage over a column of basic alumina under argon) from an addition funnel. The temperature of the reaction mixture rose from 27° C. to 61° C. during the course of the addition, and an ice bath was used to moderate the temperature rise. When, following the conclusion of the addition and removal of the cooling bath, the temperature was 32° C., the dropwise addition of 49.4 g (56.1 mL, 312 mmol) of trimethylsilyl methacrylate was begun. During the course of the addition the temperature of the reaction mixture rose to 56° C. while a total of 1.2 mL of tetrabutylammonium biacetate (0.04M in propylene carbonate) was added in 4 additions, and 20 mL of THF was added to reduce viscosity. Analysis of an aliquot of the solution by 1H NMR showed that there was no residual monomer present. After addition of 70 mL of tetrabutylammonium fluoride trihydrate (0.03M in methanol), the solution was refluxed for 12 hr. The solution was concentrated under reduced pressure with a rotary evaporator to give 80 g of a 40.58% solids solution of poly ω-2-β-dimethylaminoethyl isobutyrate(2-dimethylaminoethyl methacrylate [9 mol %]-co-n-butyl methacrylate [32 mol %]-b-methacrylic acid [59 mol %]).

Workup

  1. custompurified by passage over a column of basic alumina under argon) from an addition funnel
  2. additionThe temperature of the reaction mixture rose from 27° C. to 61° C. during the course of the addition, and an ice bath
  3. additionthe conclusion of the addition and removal of the cooling bath
  4. customwas 32° C.
  5. additionDuring the course of the addition the temperature of the reaction mixture
  6. additionwas added
  7. temperaturethe solution was refluxed for 12 hr
  8. concentrationThe solution was concentrated under reduced pressure with a rotary evaporator

Sources & evidence

ORD record
ord-5d9a79f8b5a54807bd761d9266e4f5cb
Source dataset
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05272201

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes