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

HRID 31221Notes

Reaction equation

HRID 31221 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-0374b5c1e4a849139f388984c5e71b8c
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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