6-Methoxy-alpha-tetralone → 6-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

HRID 974777Notes

Reaction equation

HRID 974777 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>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

3

Reactant 1

HCID 141126-Methoxy-alpha-tetralone

Product 1

HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-methoxy-1-tetralone (5 g, 28.4 mmol) in acetic acid (50 ml) and 48% bromhydric acid (25 ml) was heated at reflux for 7 hours. After extraction with CH2Cl2 and evaporation, the residue was purified by flash chromatography (AcoEt/petroleum ether 45/55) to give 6-hydroxy-1-tetralone as a foam (3.9 g; 84.7%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 hours
  3. extractionAfter extraction
  4. customwith CH2Cl2 and evaporation
  5. customthe residue was purified by flash chromatography (AcoEt/petroleum ether 45/55)

Sources & evidence

ORD record
ord-2d8a9fc12afa4e14b139947e00fdd672
Source dataset
uspto-grants-1997_03
Patent number
US05607928

Reaction notes

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