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

HRID 593306Notes

Reaction equation

HRID 593306 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>[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)-naphthalenoneYield 86.8%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Aqueous HBr (100 mL) was added to 6-methoxy-1-tetralone (10.0 g, 56.8 mmol), and the reaction mixture was refluxed for overnight. The reaction mixture was then brought to room temperature and extracted with ethyl acetate (2×100 mL). The organic layer was dried over sodium sulphate, filtered and removed under reduced pressure. The crude product was purified using flash chromatography using 40% ethyl acetate in hexanes to afford title compound (8.0 g, 86%) as solid. 1H NMR (400 MHz, CDCl3): δ 7.99 (d, J=8.0 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.69 (s, 1H), 6.23 (bs, 1H), 2.9 (t, J=6.0 Hz, 2H), 2.62 (t, J=6.0 Hz, 2H), 2.11 (m, 2H); ESI-MS m/z=163 (M+H)+.

Workup

  1. temperaturethe reaction mixture was refluxed for overnight
  2. customwas then brought to room temperature
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. filtrationfiltered
  6. customremoved under reduced pressure
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-d7274a06c5034a1aaa2f64db43dfc2e9
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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