Water → 6-fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

HRID 649531Notes

Reaction equation

HRID 649531 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2OC(C#N)[CH2:8][C:7](=[O:13])[C:6]=2[CH:14]=1.[OH2:15].[C:16]([O:19]CC)(=[O:18])[CH3:17]>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][CH:17]([C:16]([OH:19])=[O:18])[CH2:8][C:7](=[O:13])[C:6]=2[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 139360026-Fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carbonitrile

Product 1

HCID 27785256-fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carboxylic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 6-fluoro-3,4-dihydro-4-oxo-2H-1-benzopyran-2-carbonitrile (78.3 g, 0.41 mol)(obtained through the process as described in said Item (c) in 760 ml of concentrated hydrochloric acid was heated at reflux temperature for 50 minutes. After cooling the reaction solution, 700 ml of water and 1 liter of ethyl acetate were added to carry out an extraction. Resulting organic layer was evaporated in vacuo to dryness. To the residue, 700 ml of saturated sodium biscarbonate was added and stirred for 30 minutes. The aqueous basic solution was washed with 500 ml of ethyl acetate, acidified with 6N-hydrochloric acid and extracted with 1 liter of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to give 76.9 g (89.3%) of the desired compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 50 minutes
  3. additionwere added
  4. extractionan extraction
  5. customResulting organic layer was evaporated in vacuo to dryness
  6. additionTo the residue, 700 ml of saturated sodium biscarbonate was added
  7. washThe aqueous basic solution was washed with 500 ml of ethyl acetate
  8. extractionextracted with 1 liter of ethyl acetate
  9. washThe organic layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-df0e94c0541241cabf74efc9995856ad
Source dataset
uspto-grants-1988_04
Patent number
US04740517

Reaction notes

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