Hydrogen Bromide → 6-hydroxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one

HRID 1455024Notes

Reaction equation

HRID 1455024 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][CH2:6]2.Br>O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 107533116-Methoxy-2-phenyl-tetralone

Product 1

HCID 179785426-hydroxy-2-phenyl-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialEthyl acetate was dried
  3. customevaporated
  4. customThe product was recrystallised from toluene

Sources & evidence

ORD record
ord-81cf9bceab1748eaae09890d0db8609d
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

Loading…