Triethylamine → Acenaphthenyl methacrylate

HRID 1509795Notes

Reaction equation

HRID 1509795 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[C:9]([CH3:11])=[CH2:10].[OH:14][CH:15]1[C:25]2=[C:26]3[C:21](=[CH:22][CH:23]=[CH:24]2)[CH:20]=[CH:19][CH:18]=[C:17]3[CH2:16]1>C1(C)C=CC=CC=1>[C:8]([O:14][CH:15]1[C:25]2=[C:26]3[C:21](=[CH:22][CH:23]=[CH:24]2)[CH:20]=[CH:19][CH:18]=[C:17]3[CH2:16]1)(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 22750(+-)-Acenaphthenol

Product 1

HCID 59217557Acenaphthenyl methacrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With stirring and ice cooling, 111 g of triethylamine was added to a mixture of 120 g of methacrylic acid chloride, 170 g of 1-hydroxyacenaphthene, and 1500 g of toluene. The mixture was stirred at room temperature for 16 hours. By standard aqueous work-up and solvent distillation, a crude product was obtained. It was purified by column chromatography, yielding the target compound, acenaphthenyl methacrylate.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. distillationBy standard aqueous work-up and solvent distillation
  3. customa crude product was obtained
  4. customIt was purified by column chromatography

Sources & evidence

ORD record
ord-ae64aa7a3d984973aede869ee298bb67
Source dataset
uspto-grants-2012_07
Patent number
US08211618B2

Reaction notes

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