Hydrochloric Acid → 4-Methyl-4'-nitrobenzophenone

HRID 1358810Notes

Reaction equation

HRID 1358810 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C(=S)=S.O>[CH3:23][C:17]1[CH:22]=[CH:21][C:20]([C:12]([C:11]2[CH:15]=[CH:16][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=2)=[O:13])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2191314-Methyl-4'-nitrobenzophenoneYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

Aluminum chloride (9.3 g) was added in a single portion to a mixture of 4-nitrobenzoyl chloride (10 g) and toluene (6.3 mL) dissolved in carbon disulfide (35 mL). The mixture was warmed from room temperature to reflux and heated for 3 hours. Concentrated hydrochloric acid (19 mL) was slowly added, and the mixture stirred for an additional 30 minutes, poured into water, and extracted with dichloromethane (3X). The extract was washed with dilute ammonium hydroxide and water, dried (Na2SO4), and evaporated. Recrystallization from ethyl acetate gave 4-(4-methylbenzoyl)-nitrobenzene (10.6 g, 82%) as a pale yellow solid, m.p. 122.4-123.1° C.

Workup

  1. temperatureto reflux
  2. temperatureheated for 3 hours
  3. extractionextracted with dichloromethane (3X)
  4. washThe extract was washed with dilute ammonium hydroxide and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e05b6139bbb5433691c2458e3b20f597
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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