Acetone → 4-Allyloxybenzophenone

HRID 876070Notes

Reaction equation

HRID 876070 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][C:23]([CH3:25])=O.C(Br)C=C>O>[CH2:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][CH:15]=1)[CH:23]=[CH2:22]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 143474-Hydroxybenzophenone

Product 1

HCID 2579104-AllyloxybenzophenoneYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To start with, a three-necked flask was charged with commercially available 4-hydroxybenzophenone (39.6 g) and potassium carbonate (28 g), followed by argon substitution. Subsequently, dehydrated acetone (120 ml) was added, followed by well stirring, and then allyl bromide (18.6 ml) was added. Stirring was performed at 60° C. for 8 hours. After that, the mixture was cooled to a room temperature, and pure water was added, followed by stirring. Extraction with diethylether (100 ml) was performed twice. Extraction-and-washing with a 10% NaOH solution (100 ml) was performed twice, followed by drying over sodium sulfate. The solvent was removed by using an evaporator to obtain a pale yellow residue. The residue was recrystallized from methanol, followed by suction filtration, and then drying in vacuum was performed to obtain 4-allyloxybenzophenone (hereinafter referred to as ABP) which was a pure product (weight: 43.7 g, yield: 91.9%).

Workup

  1. stirringStirring
  2. stirringby stirring
  3. extractionExtraction with diethylether (100 ml)
  4. extractionExtraction-
  5. wash-washing with a 10% NaOH solution (100 ml)
  6. dry with materialby drying over sodium sulfate
  7. customThe solvent was removed
  8. customan evaporator
  9. customto obtain a pale yellow residue
  10. customThe residue was recrystallized from methanol
  11. filtrationfollowed by suction filtration
  12. customdrying in vacuum

Sources & evidence

ORD record
ord-6465e18953624be38c81c6114da4c063
Source dataset
uspto-grants-2015_03
Patent number
US08986488B2

Reaction notes

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