Anisole → 4-Propanoylanisole

HRID 1925579Notes

Reaction equation

HRID 1925579 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([O:11][CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:13](Cl)(=[O:16])[CH2:14][CH3:15]>ClCCl>[CH3:12][O:11][C:5]1[CH:10]=[CH:9][C:8]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 671444-PropanoylanisoleYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

While 49.3 g (370 mmol) of aluminium chloride were added to 200 ml of dichloromethane and stirred, 40 g (370 mmol) of anisole were slowly added in droplets at 5° C. Subsequently, 32 ml (370 mmol) of propionyl chloride were slowly added in droplets for 30 min, and stirring was further continued at room temperature for 2 hr. After the reaction was completed, the resultant reaction mixture was diluted with dichloromethane, and then washed with a saturated aqueous solution of sodium bicarbonate and water at 5° C. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Organic residue was purified with column-chromatography in which the mixture of ethyl acetate and n-hexane (1:10) were used as a eluent, thus obtaining 59.5 g (yield: 98%) of a title compound (7).

Workup

  1. stirringstirring
  2. customthe resultant reaction mixture
  3. washwashed with a saturated aqueous solution of sodium bicarbonate and water at 5° C
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customOrganic residue was purified with column-chromatography in which
  7. additionthe mixture of ethyl acetate and n-hexane (1:10)

Sources & evidence

ORD record
ord-b48c99f1bcc7423a8d411b3ff09af429
Source dataset
uspto-grants-2012_05
Patent number
US08178688B2

Reaction notes

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