Hydrochloric Acid → 4-Methoxy-4'-nitrobenzophenone

HRID 723543Notes

Reaction equation

HRID 723543 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([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-].Cl>C(=S)=S.O>[CH3:20][O:19][C:13]1[CH:18]=[CH:17][C:16]([C:8]([C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:9])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3477724-Methoxy-4'-nitrobenzophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

The compound of formula 3a was prepared according to the procedure of Shani, J. et al., J. Med. Chem, 1985, 28, 1504. Thus, a mixture of 4-nitrobenzoyl chloride (90 g, 0.48 mol) and anisole (57.24 g, 0.53 mol) in carbon disulfide (450 mL) was stirred in a three neck round bottom flask equipped with nitrogen inlet, condenser and mechanical stirrer that was being cooled in an ice bath. Aluminum chloride (84.0 g, 0.63 mol) was added in portions and stirring continued at ice bath temperature for 30 minutes, then at room temperature for an additional 1 hour. The reaction mixture was cooled, treated with concentrated hydrochloric acid (150 mL), diluted with cold water (250 mL). The product was collected, filtered, washed, dried, and crystallized from ethyl acetate to give 4-(4-methoxybenzoyl)-nitrobenzene as an off-white solid, m.p. 120–122° C.; Analysis for C14H11NO4: Calc.: C, 65.3; H, 4.31; N, 5.44; Found: C, 65.22; H, 4.16; N, 5.69.

Workup

  1. customequipped with nitrogen inlet, condenser and mechanical stirrer that
  2. temperaturewas being cooled in an ice bath
  3. stirringstirring
  4. customcontinued at ice bath
  5. waitat room temperature for an additional 1 hour
  6. temperatureThe reaction mixture was cooled
  7. customThe product was collected
  8. filtrationfiltered
  9. washwashed
  10. customdried
  11. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-41b5f0d2c5484177b8f638d4516db13f
Source dataset
uspto-grants-2006_11
Patent number
US07141584B2

Reaction notes

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