Hydrochloric Acid → Agn-PC-0N6mfy

HRID 262070Notes

Reaction equation

HRID 262070 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1>[CH3:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=1)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 121948722-Methyl-3-nitrobenzoyl chloride

Product 1

HCID 10562074Agn-PC-0N6mfyYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2-Methyl-3-nitrobenzoyl chloride (9.98 grams; 0.05 mole) was dissolved in 35 mls. of dry benzene and the solution was added to a slurry of aluminum chloride (13.3 grams; 0.10 mole) in 40 mls. of dry benzene over a period of 10 minutes. The resulting reaction mixture was stirred at room temperature for 21/2 hours, then heated at reflux for 2 hours and cooled to room temperature. The cooled reaction mixture was poured into 200 mls. of dilute hydrochloric acid, stirred for about 15 minutes and allowed to settle. The organic phase was separated and the aqueous phase was back extracted with 200 mls. of benzene. The benzene layer was separated and combined with the organic phase and the combined solution was washed successively with water, a dilute aqueous solution of sodium carbonate, and water. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and distilled to obtain 2-methyl-3-nitrobenzophenone (11.45 grams; 95% yield; b.p. 183° C. at 2 mm; m.p. 42° C. after recrystallization from

Workup

  1. customThe resulting reaction mixture
  2. temperatureheated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled to room temperature
  5. customThe cooled reaction mixture
  6. additionwas poured into 200 mls
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was back extracted with 200 mls
  9. customThe benzene layer was separated
  10. washthe combined solution was washed successively with water
  11. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated
  14. distillationdistilled

Sources & evidence

ORD record
ord-e57f963544a64e41811c263706ba1f54
Source dataset
uspto-grants-1979_05
Patent number
US04153632

Reaction notes

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