Hydrochloric Acid → 4-Methyl-4'-nitrobenzophenone

HRID 2121024Notes

Reaction equation

HRID 2121024 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 (3×). 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 (3×)
  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-4b691da858cd43868a2cc26b41ec7474
Source dataset
uspto-grants-2004_02
Patent number
US06693200B2

Reaction notes

Loading…