Water → 8-Fluoro-3,4-dihydro-5-methoxy-1(2H)-naphthalenone

HRID 374657Notes

Reaction equation

HRID 374657 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[CH:7]=1.O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]2[C:7]=1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 118060004-(5-Fluoro-2-methoxyphenyl)butanoic acid

Product 1

HCID 108563538-Fluoro-3,4-dihydro-5-methoxy-1(2H)-naphthalenone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

4-(5-Fluoro-2-methoxy phenyl)butanoic acid (15 g) was mixed with polyphosphoric acid (60 g) and stirred with an overhead stirrer. The reaction mixture was heated to 90° C. and stirred at this temperature for 45 minutes. The reaction mixture was allowed to cool, water (100 ml) and ethyl acetate (100 ml) were added. The mixture was neutralised with sodium hydrogen carbonate solution, the organic phase was collected. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the crude product. This material was recrystallised from hexane-15% ethyl acetate to give the clean product.

Workup

  1. stirringstirred at this temperature for 45 minutes
  2. temperatureto cool
  3. customthe organic phase was collected
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×100 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f4013b1393544018ba1b01619748807
Source dataset
uspto-grants-1996_01
Patent number
US05480873

Reaction notes

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