(3E)-4-(4-Methoxyphenyl)-3-buten-2-one → HCID 23051855, compound

HRID 1651354Notes

Reaction equation

HRID 1651354 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.O.[C:15]([OH:19])(=[O:18])[CH:16]=O>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])/[CH:12]=[CH:16]/[C:15]([OH:19])=[O:18])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 736889(3E)-4-(4-Methoxyphenyl)-3-buten-2-oneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 23051855HCID 23051855, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 17 g (96 mmol) of (E)-4-(4-methoxyphenyl)but-3-en-2-one and 8.9 g (96 mmol) of glyoxylic acid monohydrate in 25 ml of glacial 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 methylene chloride/ether/hexane yielded (E,E)-6-(4-methoxyphenyl)-4-oxo-2,5-hexadienoic acid of melting point 138°-139°.

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 methylene chloride/ether/hexane

Sources & evidence

ORD record
ord-03be2387b349408ebce9b1947970099f
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

Loading…