Benzoyl chloride → 4-Methoxybenzophenone

HRID 1194582Notes

Reaction equation

HRID 1194582 reaction equation
[Cl-].[Li+].[Cl-].[Al+3].[Cl-].[Cl-].[C:7]1([O:13][CH3:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClC(Cl)C>[CH3:14][O:13][C:7]1[CH:12]=[CH:11][C:10]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:22])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 7519AnisoleHCID 433294Lithium ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 691464-MethoxybenzophenoneYield 90.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

To an agitated mixture of lithium chloride (3.18 g., 0.075 mole) and aluminium chloride (20 g., 0.15 mole) in dichloroethane cooled to below -10° C. was added anisole (5.41 g., 0.05 mole) and benzoyl chloride (7.03 g., 0.05 mole) in dichloroethane (10 ml). The reaction mixture was held below -10° C. for one hour then allowed to come to room temperature overnight. The 4-methoxybenzophenone produced (9.55 g., 90.1% yield) had a gas chromatograph/mass spectrometer estimated purity of over 95% with 2% ortho isomers.

Workup

  1. temperaturecooled to below -10° C.
  2. waitto come to room temperature overnight

Sources & evidence

ORD record
ord-bc1a067b92d6465a8ebda1cc524cdad6
Source dataset
uspto-grants-1989_03
Patent number
US04814508

Reaction notes

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