Benzoyl chloride → 4-Methoxybenzophenone

HRID 1769922Notes

Reaction equation

HRID 1769922 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-]>CCCCCC>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:16])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7519AnisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 691464-Methoxybenzophenone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Anisole (10.8 grams, 0.1 mole) and benzoyl chloride (14 grams, 0.1 mole) were dissolved in 200 milliliters of hexane and stirred at room temperature. Anhydrous aluminum chloride, 15 grams, was added slowly to the reaction mixture over a period of 15 minutes. The reaction mixture was stirred an additional 15 minutes. The hexane was decanted and the resulting viscous residue was carefully hydrolyzed with 200 milliliters of a mixture of ice and dilute hydrochloric acid. The organic fraction was taken up in dichloromethane and the resulting solution was washed with water. Dichloromethane was removed on a rotary evaporator leaving an oil product that solidified on standing. The solidified product was broken-up, washed with two 50 milliliter portions of pentane, and dried, yielding 4-methoxybenzophenone.

Workup

  1. stirringThe reaction mixture was stirred an additional 15 minutes
  2. customThe hexane was decanted
  3. washthe resulting solution was washed with water
  4. customDichloromethane was removed on a rotary evaporator
  5. customleaving an oil product that
  6. washwashed with two 50 milliliter portions of pentane
  7. customdried

Sources & evidence

ORD record
ord-7d48425465ef427da667c47fc2ba23e0
Source dataset
uspto-grants-1995_01
Patent number
US05384077

Reaction notes

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