Ethanol → (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoic acid

HRID 16650Notes

Reaction equation

HRID 16650 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:27])/[CH:12]=[CH:13]/[C:14](/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:15]/[C:16]([O:18]CC)=[O:17].C(O)C.C(=O)(O)[O-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11](=[O:27])/[CH:12]=[CH:13]/[C:14](/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:15]/[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 86603588ethyl (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoate

Product 1

HCID 10315067(2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.45 g (1.22 mmol) of ethyl (2Z, 4E)-6-(2,5-dimethoxyphenyl)-6-oxo-3-phenylhexa-2,4-dienoate, 20 ml of ethanol, 0.206 g (2.44 mmol) of sodium bicarbonate and 20 ml of water are mixed together and refluxed for three hours. After evaporating off the solvents, the residue is poured into water, acidified with normal hydrochloric acid solution and extracted with dichloromethane. The organic phase is dried (Na2SO4), the solvent is evaporated off and the pasty product obtained is purified by flash chromatography (20/80 heptane/ethyl acetate) (yellow solid; diisopropyl ether; m.p.: 165° C.; 170 mg) and recrystallized (10/6 hexane/ethyl acetate) (0.3 g of yellow solid; 22%).

Workup

  1. temperaturerefluxed for three hours
  2. customAfter evaporating off the solvents
  3. additionthe residue is poured into water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. customthe solvent is evaporated off
  7. customthe pasty product obtained
  8. customis purified by flash chromatography (20/80 heptane/ethyl acetate) (yellow solid; diisopropyl ether; m.p.: 165° C.; 170 mg)
  9. customrecrystallized (10/6 hexane/ethyl acetate) (0.3 g of yellow solid; 22%)

Sources & evidence

ORD record
ord-189c6d88a5b14dd6bb114ca526855fb8
Source dataset
uspto-grants-2010_06
Patent number
US07737176B2

Reaction notes

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