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

HRID 1656810Notes

Reaction equation

HRID 1656810 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.Br>O>[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

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 141126-Methoxy-alpha-tetralone

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g of 6-methoxy-1-tetralone, 200 ml of acetic acid and 400 ml of hydrobromic acid (47% HBr) was heated under reflux for 24 hours. After cooling, the reaction mixture was poured into 3 liters of water, solid matter was filtered out, and the resulting filtrate was extracted three times with ethyl acetate. The extracts were washed with an aqueous solution of sodium carbonate, dried over sodium sulfate and evaporated. The resulting residue together with the filtered solid matter was recrystallized from ethyl acetate to yield 40.75 g (89.5% of the theoretical yield) of 6-hydroxy-1-tetralone in the form of reddish-brown crystals melting at 153°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter cooling
  4. filtrationwas filtered out
  5. extractionthe resulting filtrate was extracted three times with ethyl acetate
  6. washThe extracts were washed with an aqueous solution of sodium carbonate
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe resulting residue together with the filtered solid matter was recrystallized from ethyl acetate
  10. customto yield 40.75 g (89.5% of the

Sources & evidence

ORD record
ord-d662bc7414e9457d8b713bd442341c83
Source dataset
uspto-grants-1993_10
Patent number
US05254731

Reaction notes

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