Acetic Acid → HCID 23051856, compound

HRID 1651358Notes

Reaction equation

HRID 1651358 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[C:16]([OH:19])(=[O:18])[CH3:17]>O>[O:13]=[C:11](/[CH:10]=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=1)/[CH:12]=[CH:17]/[C:16]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 57088533-Buten-2-one,4-(4-CF3-phenyl)-

Product 1

HCID 23051856HCID 23051856, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12 g (56 mmol) of (E)-4-(4-trifluoromethylphenyl)but-3-en-2-one and 5.15 g (56 mmol) of glyoxlic acid monohydrate in 14 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 ether/hexane yielded (E,E)-4-oxo-6-(4-trifluoromethylphenyl)-2,5-hexadienoic acid of melting point 192°-195°.

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 ether/hexane

Sources & evidence

ORD record
ord-94cf647e57334ea3a92873742405d4fc
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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