Anisole → 4-Methoxy-4'-nitrobenzophenone

HRID 249282Notes

Reaction equation

HRID 249282 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([O:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:24][O: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

5

Reactant 3

HCID 7519AnisoleHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3477724-Methoxy-4'-nitrobenzophenoneYield 55.2%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

150 ml of nitrobenzene were cooled in an ice-bath and treated portionwise with 41 g of aluminium chloride. In so doing, the temperature was held at below 5°. Subsequently, a solution of 50 g of 4-nitrobenzoyl chloride in 50 ml of nitrobenzene was added dropwise in such a manner that the temperature remains at below 5°. At the same temperature there were added dropwise 27.8 g of anisole. Subsequently, the mixture was stirred at 20° overnight. The solution was poured on to 1 liter of ice-water, extracted with methylene chloride, dried over magnesium sulphate and concentrated. The nitrobenzene was distilled off in a high vacuum and the yellowish crystals which remained were recrystallized from cyclohexane. There were obtained 36.5 g (52%) of 4-methoxy-4'-nitrobenzophenone as a yellow solid; m.p. 124°.

Workup

  1. customwas held at below 5°
  2. customremains at below 5°
  3. extractionextracted with methylene chloride
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. distillationThe nitrobenzene was distilled off in a high vacuum
  7. customthe yellowish crystals which remained were recrystallized from cyclohexane

Sources & evidence

ORD record
ord-4897724c8f674c088324d309d32abc0e
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

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