Phenylacetic Acid → 7-Hydroxyisoflavone

HRID 1296872Notes

Reaction equation

HRID 1296872 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:9]1([CH2:15][C:16]([OH:18])=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.B(F)(F)F.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:29]N(C=O)C>>[OH:2][C:1]1[CH:3]=[C:4]2[C:6]([C:16](=[O:18])[C:15]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:29][O:5]2)=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 999Phenylacetic AcidHCID 5054ResorcinolHCID 6228Dimethylformamide2×HCID 6356Boron trifluorideHCID 24819Phosphorus pentachloride

Product 1

HCID 53768917-HydroxyisoflavoneYield 91%

Conditions

Temperature
60 °C

Procedure

Resorcinol (0.66 g, 6 mmol), phenylacetic acid (0.816 g, 6 mmol), and boron triflouride diethyletherate (5 ml) were heated to 85° C. for 90 mins. After this time the reaction was cooled and DMF (4 ml) was added. 30 min prior to the completion of the first stage, PCl5 (1.878 g, 9 mmol) was added to cool DMF (8 ml) and the mixture heated (60° C.) for 20 minutes. This was added to the solution from stage one, and the combined solution allowed to stir at room temperature for 1 hour. The reaction mixture was then poured into 1MHCl (100 ml). The precipitate formed was filtered and re-crystallized from methanol to give 7-Hydroxy-3-phenyl-chromen-4-one as a white solid (1.3 g, 91.0%); Rf 0.25 ethyl acetate/hexane (30/70)].

Workup

  1. temperatureAfter this time the reaction was cooled
  2. additionThe reaction mixture was then poured into 1MHCl (100 ml)
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. customre-crystallized from methanol

Sources & evidence

ORD record
ord-12e04ad8577546ddbc2a4342e5b60285
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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