1,4-Dioxane → HCID 86755012, compound

HRID 848946Notes

Reaction equation

HRID 848946 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][CH2:16][C:17](C)=[CH:18][CH3:19])(=[O:14])[C:11]([CH3:13])=[CH2:12].O1CCOC[CH2:22]1>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][CH2:16][CH:17]=[C:18]([CH3:19])[CH3:22])(=[O:14])[C:11]([CH3:13])=[CH2:12]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 624534-VinylphenolHCID 54547253HCID 54547253, compound

Product 1

HCID 86755012HCID 86755012, compound

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
20 °C

Procedure

A 1-liter flask was charged with 72.1 g (0.60 mol) of 4-hydroxystyrene, 49.2 g (0.60 mol) of 2-methyl-2-butenyl methacrylate, 1.5 g (0.009 mol) of azobisisobutyronitrile and 300 ml of dioxane, and the mixture was stirred for 20 hours at 20° C. 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 solids were dissolved in 300 ml of acetone, and the solution was poured into 4 liters of n-hexane to collect precipitate formed by filtration (reprecipitation process). This reprecipitation process was repeated 3 times, and the resultant precipitate was then dried to obtain 103.5 g of a 4-hydroxystyrene/3-methyl-2-butenyl methacrylate copolymer. The GPC analysis of the copolymer thus obtained revealed that its Mw was 8,800. Besides, the 1H-NMR spectrum analysis of the polymer revealed that the copolymerization ratio of 4-hydroxystyrene to 3-methyl-2-butenyl methacrylate was 53/47.

Workup

  1. customThe resultant reaction mixture
  2. customformed
  3. filtrationwas collected by filtration
  4. dissolutionThe resultant solids were dissolved in 300 ml of acetone
  5. additionthe solution was poured into 4 liters of n-hexane
  6. customto collect precipitate
  7. customformed by filtration (reprecipitation process)
  8. dry with materialthe resultant precipitate was then dried

Sources & evidence

ORD record
ord-c94d405612da427392e87b6399118675
Source dataset
uspto-grants-2000_01
Patent number
US06010826

Reaction notes

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