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

HRID 1721675Notes

Reaction equation

HRID 1721675 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.Br>C(O)(=O)C>[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 260Hydrogen BromideHCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneYield 71.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 6-methoxytetralone (8.8 g, 50 mmol) and 48% hydrobromic acid (25 mL) in acetic acid (25 mL) was refluxed at 125° C. for 3 hours. The mixture was then poured into ice/water and extracted with ethyl acetate (125 mL). The extract was washed with water and brine, dried over MgSO4, and concentrated in vacuo. To the residue was added CH2Cl2 (25 mL), and the suspension was cooled at 0° C. for 2 hours. The solid was filtered and washed with cold CH2Cl2 to afford 5.8 g of 6-hydroxytetralone.

Workup

  1. extractionextracted with ethyl acetate (125 mL)
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. additionTo the residue was added CH2Cl2 (25 mL)
  6. temperaturethe suspension was cooled at 0° C. for 2 hours
  7. filtrationThe solid was filtered
  8. washwashed with cold CH2Cl2

Sources & evidence

ORD record
ord-0e3ebc07600f40dd96cd401ffd757268
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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