Phosphate → HCID 70374065, compound

HRID 1651369Notes

Reaction equation

HRID 1651369 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:18])/[CH:12]=[CH:13]\[C:14]([O:16]C)=[O:15])=[CH:5][CH:4]=1.[OH-].[K+].P([O-])([O-])([O-])=O.C(OCC)(=O)C>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11](=[O:18])/[CH:12]=[CH:13]\[C:14]([OH:16])=[O:15])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 1061PhosphateHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 70374452HCID 70374452, compound

Product 1

HCID 70374065HCID 70374065, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.70 g (6.9 mmol) of methyl (2Z,5E)-6-(4-methoxyphenyl)-4-oxo-2,5-hexadienoate in 20 ml of ether was treated while cooling with ice and stirring vigorously within about 15 minutes with 20 ml of 5% potassium hydroxide solution. The reaction mixture was stirred at 4° for 1 hour and then treated with 15 ml of phosphate buffer (pH=6.5) and 30 ml of ethyl acetate, whereupon the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and evaporated. The solid residue was recrystallized from ethyl acetate/hexane and there was obtained (2Z,5E)-6-(4-methoxyphenyl)-4-oxo-2,5-hexadienoic acid as an orange colored powder of melting point 103.5°-104°.

Workup

  1. temperaturewhile cooling with ice
  2. customwere separated
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2e097515e16743e3a7347a9b44dea2a5
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

Loading…