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

HRID 22265

Reaction equation

HRID 22265 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 70.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Methoxytetralone (50 g, 280 mmol) was suspended in glacial acetic acid (250 mL). Hydrobromic acid (47%; 500 mL) was added and the mixture was heated at reflux for 6 h, cooled to room temperature, and poured onto 500 g of crushed ice. After 1 h the precipitate was collected and recrystalized from ethanol to provide 32 g of 6-hydroxytetralone. Concentration of the mother liquor provided an additional 9 g of product, mp 149°-152° C.; 1H NMR (CDCl3) δ7.80 (d, 1H), 6.78 (d, 1H), 6.68 (s, 1H), 2.90 (t, 2H), 2.55 (t, 2H), 2.05 (m, 2H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h
  3. customAfter 1 h the precipitate was collected
  4. customrecrystalized from ethanol

Sources & evidence

ORD record
ord-0f99e83e5e2f457eb3b0a0687ff30e0e
Source dataset
uspto-grants-1995_06
Patent number
US05428040

Linked notes

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