Sodium Acetate → HCID 22065264, compound

HRID 1715870Notes

Reaction equation

HRID 1715870 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:21])[CH:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:20])[CH:14]=1)[CH2:11]Br.[C:22]([O-:25])(=O)[CH3:23].[Na+]>CO>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:21])[C:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([OH:20])[CH:14]=1)=[CH2:11].[OH:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9](=[O:21])[CH:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]([C:4]3[CH:5]=[CH:23][C:22]([OH:25])=[C:2]([OH:1])[CH:3]=3)[O:1]2)=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 22065267HCID 22065267, compound

Product 2

HCID 22065264HCID 22065264, compoundHCID 22065272HCID 22065272, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

0.157 g of 1-(2,4-dihydroxyphenyl)-2-(3′,4′-dihydroxyphenyl)-1-oxo-3-bromo-propane, the major product of step 3 in Example 3, and about 2 molar equivalents of sodium acetate ware mixed with 88 mL of methanol and heated at about 60° C. for 4 hours. After cooling, the mixture was acidified to pH 5 and the methanol was removed under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and the solution was washed with water and concentrated. The crude product was separated by column chromatography to yield approximately equal amounts of 1-(2,4-dihydroxyphenyl)-2-(3′,4′-dihydroxy-phenyl)-1-oxo-2-propene and 7-hydroxy-(3′,4′-dihydroxyphenyl)-2,3-dihydroisoflavone.

Workup

  1. temperatureAfter cooling
  2. customthe methanol was removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washthe solution was washed with water
  5. concentrationconcentrated
  6. customThe crude product was separated by column chromatography

Sources & evidence

ORD record
ord-67a94247ba7245fcbfc1d60abe5c32c2
Source dataset
uspto-grants-2010_09
Patent number
US07799955B2

Reaction notes

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