Triethylamine → 9H-Fluoren-9-yl 2-methylprop-2-enoate

HRID 2096097Notes

Reaction equation

HRID 2096097 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[C:9]([CH3:11])=[CH2:10].[OH:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2>C1(C)C=CC=CC=1>[C:8]([O:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 74318Fluoren-9-ol

Product 1

HCID 222368199H-Fluoren-9-yl 2-methylprop-2-enoate

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, 182 g of 9-hydroxyfluorene, 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, 9-fluorenyl 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-c7531710d85e458e9f5f60f69774a79e
Source dataset
uspto-grants-2013_05
Patent number
US08450042B2

Reaction notes

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