Hydrochloric Acid → 2'-Chloro-2-methoxy-5-methyl-5'-nitrobenzophenone

HRID 636035Notes

Reaction equation

HRID 636035 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:16]=1[C:17](Cl)=[O:18].Cl>C(Cl)Cl>[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:16]=1[C:17](=[O:18])[C:8]1[CH:7]=[C:6]([CH3:5])[CH:11]=[CH:10][C:9]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 77314-MethylanisoleHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 183144782'-Chloro-2-methoxy-5-methyl-5'-nitrobenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of aluminum chloride (33.3 g, 25.0 mmol) in methylene chloride is cooled to about 5° C., treated over one hour with p-methylanisole (31.6 g, 25.0 mmol) while maintaining the reaction mixture temperature below 10° C., treated over 20 minutes with a solution of 2-chloro-5-nitrobenzoyl chloride (50.0 g, 22.7 mmol) in methylene chloride while maintaining the reaction mixture temperature below 10° C., warmed to and stirred at room temperature for 60 minutes, and poured onto ice. The resultant aqueous mixture is treated with concentrated hydrochloric acid (50 mL) and extracted with methylene chloride. The organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. After placing the solid in a Kugelrohr apparatus at 40° C. to remove residual p-methylanisole, the title product is obtained as a beige solid (68.8 g, 99.1%) which is identified by NMR spectral analyses.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 10° C.
  2. temperaturewhile maintaining the reaction mixture temperature below 10° C.
  3. temperaturewarmed to and
  4. additionpoured onto ice
  5. extractionextracted with methylene chloride
  6. extractionThe organic extract
  7. dry with materialis dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a yellow solid
  10. customat 40° C.
  11. customto remove residual p-methylanisole

Sources & evidence

ORD record
ord-e1893170dbc2415ab4f26a9dbe7ea4a4
Source dataset
uspto-grants-2001_02
Patent number
US06191275B1

Reaction notes

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