Reaktionsgleichung
Br[CH:2](Br)[C:3]1[C:4]([CH:9](Br)Br)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]1(=[O:18])[CH2:17][CH2:16][CH:15]=[CH:14]1.[I-].[Na+].Cl.[SH-].[Na+]>CN(C)C=O>[C:13]1(=[O:18])[C:17]2[CH:9]=[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]3=[CH:2][C:16]=2[CH2:15][CH2:14]1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
α,α,α′,α′-Tetrabromo-o-xylene (200 g, 0.48 mole) was dissolved in 2000 mL of dimethylformamide. 2-Cyclopentene-1-one (40 g, 0.25 mole) was added, along with 500 g sodium iodide. The mixture was heated overnight at 80° C. The mixture was cooled and poured into 2 L of ice water containing sodium bisulfide (20 g). The solids were collected and recrystallized from ethanol to give 65 g of benz[f]indan-1-one. The benzindanone was then reduced by dissolving in 600 mL of ethanol and adding 30 g of sodium borohydride, over a 2-hour period. The solution was stirred at room temperature overnight and quenched with 1 N HCl. The ethanol was removed under vacuum, and the product extracted into toluene. The product was then recrystallized from hexanes to give 58 g of benz[f]indan-1-ol. The benzindanol was then dehydrated by refluxing in 100 mL of 10% sulfuric acid overnight. The solution was cooled and extracted with toluene. The product was purified by column chromatography, in hexanes, followed by two recrystallizations from ethanol, and a final recrystallization from hexane to give 10.8 g (13% overall yield) of Benz[f]indene.
Aufarbeitung
- temperatureThe mixture was cooled
- customThe solids were collected
- customrecrystallized from ethanol
Quellen und Nachweise
- ORD-Eintrag
- ord-601b652346714710a00149f65937270c
- Quelldatensatz
- uspto-grants-2002_11
- Patentnummer
- US06479424B1
Verknüpfte Notizen
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