tert-Butyl methacrylate → HCID 22239517, compound

HRID 848945Notes

Reaction equation

HRID 848945 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[C:10]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[C:11]([CH3:13])=[CH2:12].O1CCOCC1>N(C(C)(C)C#N)=NC(C)(C)C#N.C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[C:10]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

6

Reactant 3

HCID 11448tert-Butyl methacrylateHCID 312751,4-DioxaneHCID 624534-Vinylphenol

Product 1

HCID 22239517HCID 22239517, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 7237O-XyleneSolvent

Procedure

A 500-ml flask was charged with 72.1 g (0.60 mol) of 4-hydroxystyrene, 17.1 g (0.12 mol) of t-butyl methacrylate, 1.5 g (0.009 mol) of azobisisobutyronitrile and 150 ml of dioxane, and the mixture was stirred for 100 hours at 80t in a nitrogen gas stream. The resultant reaction mixture was poured into 5 liters of xylene, and precipitate formed was collected by filtration. The resultant precipitate was dissolved in 200 ml of diethyl ether, and the solution was poured into 3 liters of n-hexane to collect precipitate formed by filtration (reprecipitation process). This reprecipitation process was repeated 3 times, and the resultant precipitate was dried to obtain 26.3 g of a 4-hydroxystyrene/t-butyl methacrylate copolymer. The GPC analysis of the polymer thus obtained revealed that its Mw was 6,410. Besides, the 1H-NMR spectrum analysis of the polymer revealed that the copolymerization ratio of 4-hydroxystyrene to t-butyl methacrylate was 71/29.

Workup

  1. customThe resultant reaction mixture
  2. customformed
  3. filtrationwas collected by filtration
  4. dissolutionThe resultant precipitate was dissolved in 200 ml of diethyl ether
  5. additionthe solution was poured into 3 liters of n-hexane
  6. customto collect precipitate
  7. customformed by filtration (reprecipitation process)
  8. dry with materialthe resultant precipitate was dried

Sources & evidence

ORD record
ord-edb8644b76ca44e99ed717121447c3e4
Source dataset
uspto-grants-2000_01
Patent number
US06010826

Reaction notes

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