Benzoyl chloride → 4-Methoxybenzophenone

HRID 974118Notes

Reaction equation

HRID 974118 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 (0.1 mole, 10.8 grams) and benzoyl chloride (0.1 mole, 14 grams) were dissolved in 200 milliliters of hexane and stirred at room temperature while 15 grams of anhydrous aluminum chloride were added slowly over a period of 15 minutes. The reaction mixture was stirred an additional 15 minutes and then the hexane decanted. The resulting viscous residue in the reaction flask was carefully hydrolyzed with 200 milliliters of a mixture of ice and dilute hydrochloric acid. The resulting organic fraction was taken up in dichloromethane and the resulting solution washed with water. Dichloromethane solvent was removed on a rotary evaporator leaving an oil product that solidified on standing. The solidified product was broken-up and washed with two 50 milliliters portions of pentane. Suction drying afforded 4-methoxybenzophenone in near quantitative yield.

Workup

  1. additionwere added slowly over a period of 15 minutes
  2. customthe hexane decanted
  3. washthe resulting solution washed with water
  4. customDichloromethane solvent was removed on a rotary evaporator
  5. customleaving an oil product that
  6. washwashed with two 50 milliliters portions of pentane
  7. customSuction drying

Sources & evidence

ORD record
ord-2805faaccd1e4fb799e7d16c5bfa81a7
Source dataset
uspto-grants-1991_11
Patent number
US05066818

Reaction notes

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