Water → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

HRID 278456Notes

Reaction equation

HRID 278456 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.O>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 962WaterHCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneYield 81.2%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

6-Methoxy-1-tetralone (80 g, 453 mmol) was taken up in 48% HBr (270 ml) at 4° C., then stirred at ambient temperature for 4 hr. Distilled H2O (1 l) was added with cooling to 4° C. and the precipitated solid was filtered, washed with H2O and recrystallised twice from EtOH-H2O (4:1) to afford 6-hydroxy-1-tetralone as a beige solid (59.7g, 368 mmol, 81%), Mp. 153-155° C., MS m/e=162.1 (M+).

Workup

  1. temperaturewith cooling to 4° C.
  2. filtrationthe precipitated solid was filtered
  3. washwashed with H2O
  4. customrecrystallised twice from EtOH-H2O (4:1)

Sources & evidence

ORD record
ord-1cc0f2ac2d9144d993cadc5b8560f307
Source dataset
uspto-grants-2002_03
Patent number
US06359138B1

Reaction notes

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