HCID 11095766, compound → HCID 23051868, compound

HRID 1651360Notes

Reaction equation

HRID 1651360 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[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]=[CH:7][C:6]([O:9][CH3:10])=[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 11095766HCID 11095766, compoundHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 23051868HCID 23051868, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 19 g (92 mmol) of (E)-4-(2,5-dimethoxyphenyl)but-3-en-2-one and 8.4 g (92 mmol) of glyoxylic acid monohydrate in 23.4 ml of acetic acid was boiled 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/ethyl acetate yielded (E,E)-6-(2,5-dimethoxyphenyl)-4-oxo-2,5-hexadienoic acid of melting point 145°-146°.

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/ethyl acetate

Sources & evidence

ORD record
ord-bc4b3a3de08b4fa9a08a7cfe5103d373
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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