Potassium Hydroxide → Bicyclo[4.2.0]octa-1,3,5,7-tetraen-7-ol

HRID 871120

Reaktionsgleichung

Reaktionsgleichung von HRID 871120
F[B-](F)(F)F.[H+].Br[CH:8]1[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:10]2[CH2:9]1.C([O-])(O)=[O:17].[Na+].[OH-].[K+]>O1CCOCC1.[Hg]=O>[C:8]1([OH:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=1

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 28118Tetrafluoroboric acidHCID 516892Sodium BicarbonateHCID 5685917-Bromobicyclo[4.2.0]octa-1,3,5-triene

Produkt 1

HCID 19963858Bicyclo[4.2.0]octa-1,3,5,7-tetraen-7-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30856Mercuric oxideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of mercury(II) oxide (591.3 mg, 2.73 mmol) and 35% aqueous tetrafluoroboric acid (TFBA) (999.4 mg, 5.46 mmol) in 1,4-dioxane (10.9 mL), 1-bromobenzocyclobutene (1.0 g, 5.46 mmol) was added. The reaction stirred at room temperature for 2 h and was then treated successively with NaHCO3 and 3N KOH until the solution remained basic. The precipitated mercury(II) oxide was filtered off and the filtrate extracted with CH2Cl2 (3×300 mL), dried with anhydrous Na2SO4, filtered, and concentrated to yield white crystals that were purified via column chromatography using a 3:2 Hexanes:EtOAc solvent system.

Aufarbeitung

  1. filtrationThe precipitated mercury(II) oxide was filtered off
  2. extractionthe filtrate extracted with CH2Cl2 (3×300 mL)
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield white crystals that
  7. customwere purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-528a77b89f2246f0a88550db901d90cf
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969622B2

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