HCID 5375764, compound → HCID 23051863, compound

HRID 1651350Notes

Reaction equation

HRID 1651350 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1/[CH:13]=[CH:14]/[C:15](=[O:17])[CH3:16].O.[C:19]([OH:23])(=[O:22])[CH:20]=O>C(O)(=O)C.O>[O:17]=[C:15](/[CH:14]=[CH:13]/[C:4]1[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1])/[CH:16]=[CH:20]/[C:19]([OH:23])=[O:22]

Participants

5

Reactant 2

HCID 5375764HCID 5375764, compoundHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 23051863HCID 23051863, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 18 g (76 mmol) of (E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one and 7 g (76 mmol) of glyoxylic acid monohydrate in 19 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/methylene chloride yielded (E,E)-4-oxo-6-(2,3,4-trimethoxyphenyl)-2,5-hexadienoic acid of melting point 125°-127°.

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/methylene chloride

Sources & evidence

ORD record
ord-23487592378f4a15adc8c59821efff4d
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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