Hydrochloric Acid → 4-(5-Fluoro-2-hydroxyphenyl)-4-oxobut-2-enoic acid

HRID 1111185Notes

Reaction equation

HRID 1111185 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1.Cl>ClCCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[C:17]([C:4](=[O:5])/[CH:3]=[CH:2]/[C:1]([OH:6])=[O:7])[CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 99874-FluoroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 145552584-(5-Fluoro-2-hydroxyphenyl)-4-oxobut-2-enoic acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Into 100 ml of 1,2-dichloroethane, maleic anhydride (11.3 g, 114 mmol) and anhydrous aluminum chloride (31.0 g, 228 mmol) were dissolved by heating at 50° C. for 15 minutes, and then p-fluoroanisole (12.6 g, 100 mmol) was added dropwise. The mixture was refluxed for an hour and then poured into 60 ml of concentrated hydrochloric acid with 400 g of cracked ice. Resulting crystals deposited out therein were obtained through a filtration, washed with water and dried in vacuo to give 16.0 g (80.0%) of the subject desired compound as yellow crystals.

Workup

  1. temperatureThe mixture was refluxed for an hour
  2. customResulting crystals
  3. customout therein were obtained through a filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give 16.0 g (80.0%) of the

Sources & evidence

ORD record
ord-03803590bf224d52942a1b5f7bdd9777
Source dataset
uspto-grants-1990_12
Patent number
US04978758

Reaction notes

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