Acetone → 4-Vinylphenol

HRID 1872289Notes

Reaction equation

HRID 1872289 reaction equation
C(O[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)C.CC(C)=[O:15]>>[CH2:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:15])=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 180AcetoneHCID 1145762-Phenylvinyl acetate

Product 1

HCID 624534-Vinylphenol

Conditions

Temperature
127.5 °C

Procedure

Acetoxystyrene (75.0 g, 0.463 mol) was placed in a 250 mL round bottom flask and purged with N2. The unimolecular initiating system 1-phenyl-1-(2',2',6',6'-tetramethyl-1'-piperidinyloxy)-ethane (1.21 g, 0.00463 mol) (with no separate free radical initiator used) was then added to the monomer. After addition of the initiator, the polymerization mixture was heated to 125-130° C., under N2, and stirred for 48 hours. During the polymerization the polymer solidified in the reaction vessel. The reaction was then cooled to room temperature and the polymer dissolved in acetone (225 mL), and isolated by precipitation into hexanes (2250 mL). The polymer was then filtered, washed with hexanes and dried in a vacuum oven at 60° C. overnight. Isolated yield was 90% of theory, Mn =8997, Mw /Mn =1.10.

Workup

  1. custompurged with N2
  2. additionwas then added to the monomer
  3. additionAfter addition of the initiator
  4. customDuring the polymerization the polymer
  5. temperatureThe reaction was then cooled to room temperature
  6. filtrationThe polymer was then filtered
  7. washwashed with hexanes
  8. customdried in a vacuum oven at 60° C. overnight
  9. customIsolated yield was 90% of theory, Mn =8997, Mw /Mn =1.10

Sources & evidence

ORD record
ord-3b6a0218912141aa99d9b7cc4ec517a7
Source dataset
uspto-grants-2000_08
Patent number
US06107425

Reaction notes

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