Glyoxylic acid, monohydrate → (E,E)-6-(4-fluorophenyl)-4-oxo-2,5-hexadienoic acid

HRID 1651351Notes

Reaction equation

HRID 1651351 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH:10]=[CH2:11])=[CH:4][CH:3]=1.[OH2:13].[C:14]([OH:18])(=[O:17])[CH:15]=O>C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:13])/[CH:11]=[CH:15]/[C:14]([OH:18])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 210992911-(4-Fluorophenyl)but-3-en-2-one

Product 1

HCID 23051853(E,E)-6-(4-fluorophenyl)-4-oxo-2,5-hexadienoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 21.5 g (131 mmol) of (E)-4-(4-fluorophenyl-but-3-en-2-one and 12 g (131 mmol) of glyoxylic acid monohydrate in 32 ml of acetic acid was heated at reflux for 20 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was extracted twice with 3N sodium hydroxide solution. The combined aqueous phases were treated with 3N hydrochloric acid to produce a strongly acidic reaction and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Crystallization of the residue from ethyl acetate/ether yielded (E,E)-6-(4-fluorophenyl)-4-oxo-2,5-hexadienoic acid of melting point 160°-162°.

Workup

  1. temperatureat reflux for 20 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe organic phase was extracted twice with 3N sodium hydroxide solution
  4. additionThe combined aqueous phases were treated with 3N hydrochloric acid
  5. customto produce
  6. customa strongly acidic reaction
  7. extractionextracted twice with ethyl acetate
  8. dry with materialThe combined organic phases were dried over magnesium sulphate
  9. concentrationconcentrated
  10. customCrystallization of the residue from ethyl acetate/ether

Sources & evidence

ORD record
ord-50c30a2a190f4b4b9987bc2a686de197
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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