Anisole → 1-(4-Methoxyphenyl)-3-methylbutan-1-one

HRID 732241Notes

Reaction equation

HRID 732241 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[Cl-].[Al+3].[Cl-].[Cl-].[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[CH3:19][O:18][C:12]1[CH:17]=[CH:16][C:15]([C:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 66054Isovaleryl chloride2×HCID 6451240Aluminum(III) Chloride

Product 1

HCID 127577691-(4-Methoxyphenyl)-3-methylbutan-1-oneYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While 40 g of isovaleryl chloride and 44 g of aluminum chloride were added to 140 ml of dichloromethane and stirred, 32.6 ml of anisole were slowly added in droplets at −10° C. or lower, and stirring was continued at room temperature for 40 min. Subsequently, 36.6 ml of isovaleryl chloride were slowly added in droplets, and stirring was further continued at room temperature for 18 hr. After the reaction was completed, the resultant reaction mixture was added with 200 ml of dichloromethane, and then washed with a saturated aqueous solution of sodium bicarbonate and water, in that order, after which the dichloromethane layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, thus obtaining 56.9 g (yield: 98.6%) of a title compound as light yellow liquid.

Workup

  1. stirringlower, and stirring
  2. stirringstirring
  3. waitwas further continued at room temperature for 18 hr
  4. customthe resultant reaction mixture
  5. washwashed with a saturated aqueous solution of sodium bicarbonate and water, in that order
  6. dry with materialafter which the dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6128e92980404ec8aa0fe45313beb7b0
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Reaction notes

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