16831-05-3 → HCID 23051874, compound

HRID 1651353Notes

Reaction equation

HRID 1651353 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[CH:11]=[CH:12]/[C:13](=[O:15])[CH3:14].O.[C:17]([OH:21])(=[O:20])[CH:18]=O>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[CH:11]=[CH:12]/[C:13](=[O:15])/[CH:14]=[CH:18]/[C:17]([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 617959916831-05-3HCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 23051874HCID 23051874, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 19 g (92 mmol) of (E)-4-(2,4-dimethoxyphenyl)but-3-en-2-one and 8.4 g (92 mmol) of glyoxylic acid monohydrate in 24 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 methylene chloride/ether/hexane yielded (E,E)-6-(2,4-dimethoxyphenyl)-4-oxo-2,5-hexadienoic acid of melting point 195°-200°.

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-c543276d6c544cedb6fddcadc3838088
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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