Hydrochloric Acid → 2,7-Bis(acryloyloxy)-9-methylfluorene

HRID 1943537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943537
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[OH:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([OH:20])=[CH:14][CH:15]=3)[CH:10]([CH3:21])[C:9]=2[CH:8]=1.C(N([CH2:27][CH3:28])CC)C.Cl.[OH-:30].[Na+].Cl[CH2:33]Cl>C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.O>[C:33]([O:6][C:7]1[CH:19]=[CH:18][C:17]2[C:16]3[C:11](=[CH:12][C:13]([O:20][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:14][CH:15]=3)[CH:10]([CH3:21])[C:9]=2[CH:8]=1)(=[O:30])[CH:27]=[CH2:28]

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 14798Sodium HydroxideHCID 219606279-methyl-9H-fluorene-2,7-diol

Produkt 1

HCID 672843372,7-Bis(acryloyloxy)-9-methylfluorene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 314042,6-Di-tert-butyl-4-methylphenolKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Acryloyl chloride (55.4 g, 612.1 mmol) was added dropwise to a mixture of dichloromethane (500 mL), 2,7-dihydroxy-9-methylfluorene (T-11) (50.0 g, 235.6 mmol), triethylamine (61.7 g, 609.7 mmol) and 2,6-di-tert-butyl-p-cresol (52.0 mg, 0.24 mmol) in an ice bath under an atmosphere of nitrogen, and then the mixture was warmed slowly to room temperature. The stirring was continued at room temperature for 16 hours, and the reaction mixture was poured into water. The organic layer was wished with 1M-hydrochloric acid, aqueous 1M-sodium hydroxide solution and water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of dichloromethane and ethanol to give colorless crystals (34.2 g) of 2,7-bis(acryloyloxy)-9-methylfluorene (1-3-4).

Aufarbeitung

  1. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  2. distillationthe organic solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent: toluene)
  4. customby recrystallization from a mixed solvent of dichloromethane and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3cc25621b2f84187a5d806add8184e5f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394468B2

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