Reaktion #59499

Reaktionsgleichung

6-Methoxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one

HBr

→

6-Hydroxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   TrocknenEthyl acetate was dried
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe product was recrystallised from toluene

Vorschrift

6-Methoxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one (1.0 g) was refluxed with 47% HBr (20 ml) until disappearance of the starting material. The mixture was poured into water and extracted with ethyl acetate. Ethyl acetate was dried and evaporated. The product was recrystallised from toluene. 1H NMR (400 MHz, d6-DMSO) δ: 10.35 (s, 1H), 7.79 (d, 1H, J 8.6 Hz), 7.15-7.33 (m, 5H), 6.75 (dd, 1H, J 8.6, 2.4 Hz), 6.68 (d, 1H, J 2.3 Hz), 3.79-3.85 (m, 1H), 2.99-3.06 (m, 1H), 2.83-2.90 (m, 1H), 2.19-2.33 (m, 2H).

Quelle