Anisole → (4-Methoxyphenyl)(3-nitrophenyl)methanone

HRID 2086770Notes

Reaction equation

HRID 2086770 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[C:13]1([O:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[Al+3].[Cl-].[Cl-].C(OCC)(=O)C>ClCCl.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([C:16]1[CH:17]=[CH:18][C:13]([O:19][CH3:20])=[CH:14][CH:15]=1)=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 7519AnisoleHCID 8495Benzoyl chloride, 3-nitro-HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-nitrobenzoyl chloride (3.71 g), anisole (2.0 ml) and aluminum chloride (2.67 g) in dichloromethane (50 ml) was refluxed for 1 hour. The reaction mixture was poured into a mixture of ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with ethyl acetate to give 1-(3-nitrobenzoyl)-4-methoxybenzene (955 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-96613a4d4c73421897afe832a6520763
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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