Phenylacetic Acid → 6-Ethyl-7-hydroxy-3-phenyl-chromen-4-one

HRID 1296875Notes

Reaction equation

HRID 1296875 reaction equation
[CH2:1]([C:3]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:4]=1O)[CH3:2].[C:11]1([CH2:17][C:18]([OH:20])=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P(Cl)(Cl)(Cl)(Cl)Cl.CN([CH:30]=[O:31])C>>[CH2:1]([C:3]1[CH:4]=[C:6]2[C:7](=[CH:8][C:9]=1[OH:10])[O:20][CH:18]=[C:17]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:30]2=[O:31])[CH3:2]

Participants

5

Reactant 4

HCID 999Phenylacetic AcidHCID 6228DimethylformamideHCID 24819Phosphorus pentachlorideHCID 98339742-Ethylresorcinol

Product 1

HCID 53996516-Ethyl-7-hydroxy-3-phenyl-chromen-4-oneYield 87.7%

Procedure

This compounds was synthesised in the same manner as described above. Ethyl resorcinol (0.83 g, 6 mmol), phenylacetic acid (0.82 g, 6 mmol), BF3Et2O (3.88 ml, 31.5 mmol), PCl5 (1.88 g, 9 mmol), DMF (4.6 ml and 10 ml). The precipitate formed was filtered and re-crystallized from methanol to give 6-Ethyl-7-hydroxy-3-phenyl-chromen-4-one as a pale brown solid (1.4 g, 87.7%); Rf 0.4 cf SM 0.5 ethyl acetate/hexane (40/60).

Workup

  1. customThis compounds was synthesised in the same manner
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customre-crystallized from methanol

Sources & evidence

ORD record
ord-61b994b139f5463fade75d10c22fc729
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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