Diphenylmethane → HCID 15123923, compound

HRID 1377231Notes

Reaction equation

HRID 1377231 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([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCCl>[N+:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([C:20]2[CH:21]=[CH:22][C:17]([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([C:12](=[O:13])[C:11]4[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:16][CH:15]=4)=[CH:28][CH:29]=3)=[CH:18][CH:19]=2)=[O:13])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 7580DiphenylmethaneHCID 85024-Nitrobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15123923HCID 15123923, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
47 °C

Procedure

In a 10-liters three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 1300 g (9.75 mole) of aluminum chloride and 4.2 liters of 1,2-dichloroethane were mixed, and 1323 g (7.13 mole) of paranitrobenzoyl chloride was introduced with ice cooling to be dissolved. After warming the reaction solution to 47° C., a solution of 500 g (2.97 mole) of diphenylmethane in 500 milliliters of 1,2-dichloroethane was added dropwise for 3 hours and 30 minutes. After the dropwise addition was ended, the solution was stirred at 50° C. for 4 hours. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was poured in 7 liters of ice water, and then extracted with 7 liters of chloroform. The solution was washed with a 6N-HCl aqueous solution, an aqueous solution of sodium hydrogencarbonate, brine and water, and then dried with magnesium sulfate. After removing off chloroform by a rotary evaporator, filtration was carried out when crystals being deposited sufficiently. Filtered substances were treated with a silica gel column and recrystallized from chloroform/ethyl acetate, to obtain 867 g of 1,1-bis(4-(4-nitrobenzoyl)phenyl)methane as crystals.

Workup

  1. customIn a 10-liters three-necked flask equipped with a stirring device
  2. dissolutionto be dissolved
  3. additionAfter the dropwise addition
  4. extractionextracted with 7 liters of chloroform
  5. washThe solution was washed with a 6N-HCl aqueous solution
  6. dry with materialan aqueous solution of sodium hydrogencarbonate, brine and water, and then dried with magnesium sulfate
  7. customAfter removing off chloroform
  8. customby a rotary evaporator, filtration
  9. additionFiltered substances were treated with a silica gel column
  10. customrecrystallized from chloroform/ethyl acetate

Sources & evidence

ORD record
ord-1d9ed6d384ce40ebaca32fa75b06f7eb
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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