Hydrogen Bromide → 1(2H)-Naphthalenone, 3,4-dihydro-6,7-dihydroxy-

HRID 2188216Notes

Reaction equation

HRID 2188216 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13]C)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Br>O>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 2668163,4-Dihydro-6,7-dimethoxy-1(2H)-naphthalenone

Product 1

HCID 6012071(2H)-Naphthalenone, 3,4-dihydro-6,7-dihydroxy-Yield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6,7-dimethoxy-3,4-dihydro-2H-naphthalene-1-one (15.0 g) and 48% aqueous hydrobromic acid (60 cm3) was heated under reflux for 18 h. Upon cooling to room temperature, water (100 cm3) was added and the resulting aqueous mass was extracted with ethyl acetate (3×100 cm3). The combined extracts were dried (Na2SO4), filtered and evaporated to dryness to leave a brown powder. This was recrystallised from acetonitrile to afford the title compound (9.4 g) as a red powder.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. extractionthe resulting aqueous mass was extracted with ethyl acetate (3×100 cm3)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto leave a brown powder
  8. customThis was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-99846a97f2274c68a46c23bba997f718
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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