Anisole → 4'-Methoxyacetophenone

HRID 2271250Notes

Reaction equation

HRID 2271250 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].S([O-])([O-])(=O)=O.[Mg+2]>[N+](C)([O-])=O.CCOCC>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:9](=[O:11])[CH3:10])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7519AnisoleHCID 7918Acetic AnhydrideHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 74764'-MethoxyacetophenoneYield 97.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6375NitromethaneSolvent

Conditions

Temperature
21 °C

Procedure

The scandium salt of dibutylaminosulfonylmalononitrile, obtained in Example 40, was used as catalyst in a Friedel-Crafts reaction of acylation, by operating in the following manner. In 40 ml of anhydrous nitromethane, there is added 570 mg (700 μmoles) of Sc(DBSM)3, and 1.08 g (10 mmoles) of anisol and 2.04 g of acetic anhydride. After stirring during 10 min at 21° C., the reaction mixture was diluted with 50 ml of ether and the reaction was inhibited by using 100 ml of a saturated solution of sodium bicarbonate NaHCO3. After filtration on Celite, the solution was extracted with three fractions of 50 ml of ether, and the collected ether phase was washed with a saturated solution of potassium chloride. After drying the ether phase with magnesium sulfate and evaporation, 1.46 g of p-methoxyacetophenone (97% yield) was recovered, with a purity characterized by a proton RMN higher than 99%.

Workup

  1. customwas used as catalyst in a Friedel-Crafts reaction of acylation
  2. filtrationAfter filtration on Celite
  3. extractionthe solution was extracted with three fractions of 50 ml of ether
  4. washthe collected ether phase was washed with a saturated solution of potassium chloride
  5. dry with materialAfter drying the ether phase

Sources & evidence

ORD record
ord-b444f9fa20334379b80f9d496487c5d9
Source dataset
uspto-grants-2001_12
Patent number
US06333425B1

Reaction notes

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