4-(2-Fluorophenyl)butanoic acid → 5-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 2257837Notes

Reaction equation

HRID 2257837 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:13]

Participants

3

Reactant 1

HCID 154910364-(2-Fluorophenyl)butanoic acid

Product 1

HCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 gm of polyphosphoric acid heated at 80° C. was added 15.9 gm of the compound prepared in (6) above over 1 hour while stirring. The stirring was continued for another 1 hour at the same temperature. The resultant reaction mixture was poured into ice-cooled water and extracted with chloroform. The extract was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 14.1 gm of the title compound.

Workup

  1. customThe resultant reaction mixture
  2. additionwas poured into ice-
  3. extractionextracted with chloroform
  4. washThe extract was washed with water and saturated brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8bb75f2d8edf4617827bf1ba2b0ea2ed
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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