Phenylacetic Acid → Benzyl 2,4-dihydroxyphenyl ketone

HRID 1296860Notes

Reaction equation

HRID 1296860 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([CH:18]=[CH:17][CH:16]=[C:14]([OH:15])[CH:13]=1)[OH:12].B(F)(F)F.CCOCC>CC([O-])=O.[Na+]>[OH:12][C:11]1[CH:13]=[C:14]([OH:15])[CH:16]=[CH:17][C:18]=1[C:8](=[O:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 5054ResorcinolHCID 8000Boron trifluoride etherate

Product 1

HCID 138005Benzyl 2,4-dihydroxyphenyl ketoneYield 87%

Reagents, catalysts & solvents 1

HCID 517045Sodium AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Phenylacetic acid (0.82 g, 6 mmol), resorcinol (0.66 g, 6 mmol), and boron trifloride etherate (4 ml, 33 mmol) were mixed together and heated to 80° C. under argon. The mixture was then poured into 10% NaOAc (100 ml) and after standing for two hours a brown solid precipitate formed. This was purified by flash chromatography to give the required compound as a white solid (1.19 g, 87%); Rf 0.5 hexane/ethyl acetate (70/30).

Workup

  1. customa brown solid precipitate formed
  2. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-54be33c3d7aa4acdaeb9068be8605a82
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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