Acryloyl chloride → HCID 22665285, compound

HRID 1007741Notes

Reaction equation

HRID 1007741 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].OC1C=CC([C:13]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH3:14])=CC=1>>[C:1]([CH2:14][C:13]([O:21][C:18]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1)([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:4])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 13140Acryloyl chlorideHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane2×

Product 1

HCID 22665285HCID 22665285, compoundYield 85%

Procedure

Acryloyl chloride (45.3 g, 0.5 mole) was dissolved in 50 g (0.63 mole) of pyridine anhydride in a reaction vessel. The exothermic reaction was cooled by placing the reaction vessel in a liquid nitrogen-isopropyl alcohol bath. Thereafter, 193 g (0.63 mole) of 1,1,1-tris(4-hydroxy phenyl)ethane was added dropwise to the reaction mixture and stirred. After the addition of 1,1,1-tris(4-hydroxy phenyl)ethane, the reaction vessel was removed from the cooling bath, and the reaction was stirred at room temperature for over 24 hours. The progress of the reaction was monitored by TLC. The reaction mixture was transferred to a separatory funnel, neutralized using 1 N aqueous sulfuric acid solution, and extracted with dichloromethane. The organic layer was washed with deionized water, concentrated under reduced pressure, and purified by distillation under reduced pressure to yield acryloyl phenoxy bis(-4-hydroxy phenyl)ethane monomer (yield 85%).

Workup

  1. customThe exothermic reaction
  2. temperaturewas cooled
  3. customthe reaction vessel was removed from the cooling bath
  4. stirringthe reaction was stirred at room temperature for over 24 hours
  5. customThe reaction mixture was transferred to a separatory funnel
  6. extractionextracted with dichloromethane
  7. washThe organic layer was washed with deionized water
  8. concentrationconcentrated under reduced pressure
  9. distillationpurified by distillation under reduced pressure

Sources & evidence

ORD record
ord-e13b4be2ff3a409c8d4e8dfe126c0c04
Source dataset
uspto-grants-2004_09
Patent number
US06797451B2

Reaction notes

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