Hydrochloric Acid → 8-fluoro-5-hydroxy-3,4-dihydro-1 (2H)-naphthalenone

HRID 1633727Notes

Reaction equation

HRID 1633727 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:13]C)=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2.[Cl-].[Al+3].[Cl-].[Cl-].Cl.ClCCl>ClCCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 6451240Aluminum(III) ChlorideHCID 108563538-Fluoro-3,4-dihydro-5-methoxy-1(2H)-naphthalenone

Product 1

HCID 112638478-fluoro-5-hydroxy-3,4-dihydro-1 (2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 8-fluoro-5-methoxytetralone (Owton, W. M. J. Chem. Soc., Perkin Trans. 1 (1994), 2131-2135) (7.0 g, 36 mmol) in 1,2-dichlorethane (150 mL) was treated with aluminum chloride-(21 g, 157 mmol), refluxed for 3.5 hours, cooled to ambient temperature, poured carefully into 4M HCl (500 mL), stirred for 16 hours, treated with dichloromethane (400 mL) and thoroughly shaken. A black solid was removed by filteration through Celite®. The dichloromethane layer was isolated, combined with the black solid and extracted with 5% sodium hydroxide solution (3×150 mL). The combined sodium hydroxide extracts were acidified with 4M hydrochloric acid and the resulting solid was collected by filtration to provide the desired product as a brown solid.

Workup

  1. temperaturerefluxed for 3.5 hours
  2. stirringthoroughly shaken
  3. customA black solid was removed by filteration through Celite®
  4. customThe dichloromethane layer was isolated
  5. extractionextracted with 5% sodium hydroxide solution (3×150 mL)
  6. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-2cb110e5901f4deb90e6543245eb31d0
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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