Water → (4-Methoxyphenyl)(4-methylphenyl)methanone

HRID 279699

Reaction equation

HRID 279699 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([C:15](O)=[O:16])=[CH:11][CH:10]=1.O>ClC1C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Hf+4].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:18])=[CH:10][CH:11]=2)=[O:16])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7470P-Toluic AcidHCID 7519Anisole

Product 1

HCID 32113(4-Methoxyphenyl)(4-methylphenyl)methanoneYield 9%

Reagents, catalysts & solvents 2

HCID 9853707Hafnium(IV) TrifluoromethanesulfonateCatalystHCID 7964ChlorobenzeneSolvent

Procedure

Hafnium (IV) trifluoromethanesulfonate (5.15 g), anisole (1.08 g) and para-toluic acid (1.36 g) were refluxed together in 125 mL chlorobenzene with azeotropic removal of the upper water layer (inverse Dean-Stark apparatus). After 3 hours, the mixture was cooled and extracted with 2×25 mL water, then 2×25 mL saturated sodium bicarbonate solution. The organic layer was dried using anhydrous sodium sulfate, filtered, then concentrated down in vacuo to give crude 4-methoxy-4′-methylbenzophenone (0.20 g, 9% yield) as a colored crystalline solid. The aqueous layer was concentrated in vacuo to give 4.41 g of a damp, white solid.

Workup

  1. temperaturethe mixture was cooled
  2. extractionextracted with 2×25 mL water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated down in vacuo

Sources & evidence

ORD record
ord-9a2ab42f81ea45869a220583f5a397ed
Source dataset
uspto-grants-2002_03
Patent number
US06362375B1

Linked notes

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