Hydrochloric Acid → Agn-PC-0N6mfy

HRID 462089Notes

Reaction equation

HRID 462089 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 189.9%

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 26 1/2 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 petroleum ether).

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-c76d538a100042bd8370a0ef1904ba44
Source dataset
uspto-grants-1977_12
Patent number
US04065477

Reaction notes

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