Benzoyl chloride → HCID 570296, compound

HRID 1377214Notes

Reaction equation

HRID 1377214 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:14]1([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[N+](C1C=CC=CC=1)([O-])=O>[C:5]([C:17]1[CH:18]=[CH:19][C:14]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:5](=[O:12])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:25][CH:26]=2)=[CH:15][CH:16]=1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7580DiphenylmethaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 570296HCID 570296, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Conditions

Temperature
70 °C

Procedure

In a 5-liter four-necked flask equipped with a stirring device, a thermometer, a condenser and a nitrogen substituting device, 317.0 g of aluminum chloride and 1.5 liters of nitrobenzene were mixed and then 209.0 g of benzoyl chloride was introduced with ice cooling to be dissolved, and then a solution of 100.0 g of diphenylmethane in 100 milliliters of nitrobenzene was added dropwise for 30 minutes. 30 minutes after the end of the dropwise adding, the temperature was increased to 70° C. by removing an ice bath, and stirring was carried out with maintaining the temperature for 5 hours. After the end of the reaction was confirmed by a gas chromatography, the reaction solution was poured on 1.0 liter of ice, and then extracted with 2.5 liters of chloroform. Thereafter, the solution was washed with a 6N-HCl aqueous solution, an aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and nitrobenzene by a rotary evaporator, and then 150.7 g of 1,1-bis(4-benzoylphenyl)methane was obtained as crystals after recrystallizing from ethyl acetate.

Workup

  1. customIn a 5-liter four-necked flask equipped with a stirring device
  2. dissolutionto be dissolved
  3. addition30 minutes after the end of the dropwise adding
  4. customby removing an ice bath
  5. temperaturewith maintaining the temperature for 5 hours
  6. additionthe reaction solution was poured on 1.0 liter of ice
  7. extractionextracted with 2.5 liters of chloroform
  8. washThereafter, the solution was washed with a 6N-HCl aqueous solution
  9. customan aqueous solution of sodium hydrogencarbonate, brine and water, removed off chloroform and nitrobenzene
  10. customby a rotary evaporator

Sources & evidence

ORD record
ord-60a7284db8df41cdb2ffffac13eb539a
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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