Boron tribromide → 6-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1859812

Reaktionsgleichung

Reaktionsgleichung von HRID 1859812
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=[O:14])[CH2:8][CH2:7][CH2:6]2

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

Produkt 1

HCID 186264826-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-oneAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 2.79 g (14.7 mmol) of 6-methoxy-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone in 150 mL of CH2Cl2 was cooled in ice and treated with 20 mL (0.22 mol) of BBr3. After stirring at 0° C. for 0.5 hour, the solution was stirred at room temperature overnight. The solution was poured into ice water and extracted with Et2O. The Et2O was extracted twice with 5% NaOH and the NaOH washed with Et2O. The NaOH solution was acidified to the Congo Red end point with dilute HCl, then extracted with Et2O. The Et2O was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure left the crude product. This was taken up in acetone and treated with charcoal. Filtering through Celite and removal of the solvent under reduced pressure left 2.08 g (80.6% yield) of the product as a brown solid. The structure was confirmed by NMR and mass spectroscopy. MS m/z 177 (M+H+).

Aufarbeitung

  1. stirringthe solution was stirred at room temperature overnight
  2. extractionextracted with Et2O
  3. extractionThe Et2O was extracted twice with 5% NaOH
  4. washthe NaOH washed with Et2O
  5. extractionextracted with Et2O
  6. washThe Et2O was washed with saturated NaCl
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent under reduced pressure
  9. waitleft the crude product
  10. additiontreated with charcoal
  11. filtrationFiltering through Celite and removal of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35ef61631d88428dbbbf96e2d83acf9d
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528535B2

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