Benzene → 1,4-Dibenzoylbenzene

HRID 333195Notes

Reaction equation

HRID 333195 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.Cl.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[C:5]([C:6]1[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:6]2[CH:14]=[CH:13][CH:9]=[CH:8][CH:7]=2)=[CH:8][CH:7]=1)(=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 7488Terephthaloyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 763951,4-DibenzoylbenzeneYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Aluminum trichloride (1.37 g, 10.33 mmol) was added to a solution of terephthaloyl dichloride (1.0 g, 4.42 mmol) in anhydrous dichloromethane and excess benzene. After stirring for 12 h at room temperature under an inert atmosphere of nitrogen gas, the reaction mixture treated with 10% HCl (50 mL) and the products were extracted with ethyl acetate (3×20 mL). The combined organic phases were washed with brine and dried over sodium sulfate. After the organic layer was concentrated under reduced pressure, purification using flash chromatography (silica gel, hexanes:ethyl acetate, 80:20) afforded 1,4-dibenzoyl benzene 1 (0.405 g, 1.41 mmol) in a 32% yield.

Workup

  1. extractionthe products were extracted with ethyl acetate (3×20 mL)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter the organic layer was concentrated under reduced pressure, purification

Sources & evidence

ORD record
ord-86786ebee3d04c0d875645291fe01509
Source dataset
uspto-grants-2014_11
Patent number
US08877967B2

Reaction notes

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