Hydrochloric Acid → HCID 22919497, compound

HRID 1377233Notes

Reaction equation

HRID 1377233 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([C:19]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>ClCCCl.[Fe](Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:16]2[CH:15]=[CH:14][C:13]([C:19]3([C:25]4[CH:26]=[CH:27][C:28]([C:8](=[O:9])[C:7]5[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=5)=[CH:29][CH:30]=4)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:18][CH:17]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 85024-Nitrobenzoyl chlorideHCID 30490Benzene, 1,1'-cyclohexylidenebis-

Product 1

HCID 22919497HCID 22919497, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

In a 10-liters three-necked flask equipped with a stirring device, a thermometer and a nitrogen substituting device, 703 g (4.33 mole) of iron chloride and 1.7 liters of 1,2-dichloroethane were mixed, and 732 g (3.94 mole) of paranitrobenzoyl chloride was introduced with ice cooling to be dissolved. After warming the reaction solution to 80° C., a solution of 395 g (1.67 mole) of diphenylcyclohexane in 630 milliliters of 1,2-dichloroethane was added dropwise for 3 hours and 40 minutes. After the dropwise addition was ended, the solution was stirred gently at reflux for 6 hours. After the end of the reaction was confirmed by a liquid chromatography, the reaction solution was poured in 2 liters of ice, 1 liter of a 4N-HCl aqueous solution was added and then extracted with 1.5 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, 700 milliliters of ethyl acetate was added still hot and cooled to deposit crystals. Deposited crystals were filtered off and the filtrate was treated with a silica gel column and purified by recrystallization from chloroform/ethyl acetate, to obtain 485 g of 1,1-bis(4-(4-nitrobenzoyl)phenyl)cyclohexane 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. temperatureat reflux for 6 hours
  5. extractionextracted with 1.5 liters of chloroform
  6. washThe solution was washed with a 6N-HCl aqueous solution
  7. dry with materialan aqueous solution of sodium hydrogencarbonate, brine and water, and then dried with magnesium sulfate
  8. customAfter removing off chloroform
  9. customby a rotary evaporator, 700 milliliters of ethyl acetate
  10. additionwas added still hot
  11. temperaturecooled
  12. filtrationDeposited crystals were filtered off
  13. additionthe filtrate was treated with a silica gel column
  14. custompurified by recrystallization from chloroform/ethyl acetate

Sources & evidence

ORD record
ord-84887b74dc8f48feaa16a00d5ac9bf66
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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