HCID 12300571, compound → HCID 23051865, compound

HRID 1651352Notes

Reaction equation

HRID 1651352 reaction equation
[CH3:1][S: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][S: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 12300571HCID 12300571, compoundHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 23051865HCID 23051865, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 10.5 g (54.6 mmol) of (E)-4-[4-(methylthio)phenyl]but-3-en-2-one and 5.02 g (54.6 mmol) of glyoxylic acid monohydrate in 15 ml of acetic acid was heated at reflux for 20 hours. The reaction mixture was diluted with water and extracted with methylene chloride. 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 methylene chloride. The combined organic phases were dried over magnesium sulphate and concentrated. Crystallization of the residue from methylene chloride/ether yielded (E,E)-6-[4-(methylthio)-phenyl]-4-oxo-2,5-hexadienoic acid of melting point 160°-163°.

Workup

  1. temperatureat reflux for 20 hours
  2. extractionextracted with methylene chloride
  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 methylene chloride
  8. dry with materialThe combined organic phases were dried over magnesium sulphate
  9. concentrationconcentrated
  10. customCrystallization of the residue from methylene chloride/ether

Sources & evidence

ORD record
ord-f19bfc4b12db48f6bb0464be39a89048
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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