Acetic Acid → 1H-2-Benzopyran-3-carboxylic acid, 4-(4-fluorophenyl)-1-oxo-

HRID 1084446Notes

Reaction equation

HRID 1084446 reaction equation
C([O:3][C:4]([C:6]1(C(OCC)=O)[C:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8](=[O:9])[O:7]1)=[O:5])C.C(O)(=O)C.Cl>O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:8](=[O:9])[O:7][C:6]=2[C:4]([OH:5])=[O:3])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20063366HCID 20063366, compound

Product 1

HCID 106130211H-2-Benzopyran-3-carboxylic acid, 4-(4-fluorophenyl)-1-oxo-Yield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 3,3-bis(ethoxycarbonyl)-4-(4-fluorophenyl)-4-hydroxy-3,4-dihydroisocoumarin (3.85 g), glacial acetic acid (40 ml) and concentrated hydrochloric acid (40 ml) was heated at reflux for 2 hours. The mixture was then cooled and poured onto a mixture of ice and water (200 ml), and the resulting solid was filtered off and washed with water, to give 4-(4-fluorophenyl)isocoumarin-3-carboxylic acid (2.65 g) in the form of a white powder, m.p.218°-220° C. [Elemental analysis: C,67.4; H,3.41; F,6.73%; calculated: C,67.6; H,3.19; F,6.68%].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe mixture was then cooled
  4. filtrationthe resulting solid was filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-7b1c191b29774baca4e2251a97eda586
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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