Potassium Permanganate → 7-Bromo-3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid

HRID 460289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460289
[Br:1][C:2]1[C:10]2[O:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=2[CH:5]=[C:4]([CH:13]=[O:14])[CH:3]=1.[O-:15][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[Br:1][C:2]1[C:10]2[O:9][CH2:8][C:7]([CH3:11])([CH3:12])[C:6]=2[CH:5]=[C:4]([C:13]([OH:15])=[O:14])[CH:3]=1

Komponenten

5

Edukt 2

HCID 516875Potassium PermanganateHCID 184454227-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde

Produkt 1

HCID 220414067-Bromo-3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acidAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde (14.61 g, 57.29 mmol) in acetone (80 mL) was added at room temperature to KMnO4 (9.05 g, 57.29 mmol) dissolved in water (200 mL). The reaction mixture was stirred at room temperature overnight filtered over celite then H2SO4 in water was added and the solution extracted with ethyl acetate. The organic layer was further washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 9.9 g of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid (64%). 1H NMR (300 MHz; CDCl3): 1.40 (s, 6H), 4.44 (s, 2H), 7.79 (s, 1H), 8.13 (s, 1H). c. 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde.

Aufarbeitung

  1. filtrationfiltered over celite
  2. additionH2SO4 in water was added
  3. extractionthe solution extracted with ethyl acetate
  4. washThe organic layer was further washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d5791ae395814665b1e6dc8ebf1efea6
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196108B2

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