Hydrochloric Acid → HCID 22919273, compound

HRID 1377234Notes

Reaction equation

HRID 1377234 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:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH3:28])[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:29]4[CH:30]=[CH:31][C:32]([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:33][CH:34]=4)[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:20]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 22919173HCID 22919173, compound

Product 1

HCID 22919273HCID 22919273, compoundYield 55%

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, 629 g (3.88 mole) of iron chloride and 1.7 liters of 1,2-dichloroethane were mixed, and 595 g (3.21 mole) of paranitrobenzoyl chloride was introduced with ice cooling to be dissolved. After warming the reaction solution to 80° C., a solution of 391 g (1.34 mole) of 1,1-diphenyl-4-butylcyclohexane in 630 milliliters of 1,2-dichloroethane was added dropwise for 3 hours and 30 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 on 2 liters of ice, and 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 dried with magnesium sulfate. After removing off chloroform by a rotary evaporator, treating with a silica gel column and purifying by recrystallization from ethyl acetate, 435 g of 1,1-bis(4-(4-nitrobenzoyl)phenyl)-4-butylcyclohexane was obtained 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. additionwas added
  6. extractionextracted with 1.5 liters of chloroform
  7. washThe solution was washed with a 6N-HCl aqueous solution
  8. dry with materialan aqueous solution of sodium hydrogencarbonate, brine and water, and dried with magnesium sulfate
  9. customAfter removing off chloroform
  10. customby a rotary evaporator
  11. additiontreating with a silica gel column
  12. custompurifying by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-999bc029187d4263a32e5cb89719f816
Source dataset
uspto-grants-1997_09
Patent number
US05663440

Reaction notes

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