Anisole → 4'-Methoxy-3-(trifluoromethyl)benzophenone

HRID 2059316Notes

Reaction equation

HRID 2059316 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](Cl)=[O:11].[C:18]1([O:24][CH3:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([C:21]1[CH:22]=[CH:23][C:18]([O:24][CH3:25])=[CH:19][CH:20]=1)=[O:11]

Participants

5

Reactant 3

HCID 7519AnisoleHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 700564'-Methoxy-3-(trifluoromethyl)benzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminium chloride (15.5 g) was added over 2 hours in small portions to an ice-cooled solution of 3-trifluoromethylbenzoyl chloride (21.7 g) and anisole (12.5 g) in dichloromethane. After a further 2 hours at room temperature, the mixture was poured on to ice, extracted with dichloromethane and the extracts washed with water and dried (MgSO4). Removal of solvent gave a solid which was recrystallised first from light petrol (b.p. 60°-80°) and then from ethanol-water, giving white prisms of the ketone, m.p. 62.5°-63.5°, (17.5 g, 60%).

Workup

  1. additionthe mixture was poured on to ice
  2. extractionextracted with dichloromethane
  3. washthe extracts washed with water
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent
  6. customgave a solid which
  7. customwas recrystallised first from light petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-f8326b6efe9f4aeb94a064599c088000
Source dataset
uspto-grants-1982_03
Patent number
US04322370

Reaction notes

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