1-Chloro-4-nitrobenzene → HCID 178447844, compound

HRID 465289

Reaction equation

HRID 465289 reaction equation
[OH-:1].[K+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)[CH2:15][CH2:14][CH:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1>CS(C)=O>[N+:39]([C:36]1[CH:37]=[CH:38][C:33]([O:3][C:4]2[CH:5]=[CH:6][C:7]([C:10]3([C:25]4[CH:26]=[CH:27][C:28]([O:31][C:33]5[CH:38]=[CH:37][C:36]([N+:39]([O-:40])=[O:1])=[CH:35][CH:34]=5)=[CH:29][CH:30]=4)[CH2:15][CH2:14][CH:13]([C@H:16]4[CH2:17][CH2:18][C@H:19]([CH2:22][CH2:23][CH3:24])[CH2:20][CH2:21]4)[CH2:12][CH2:11]3)=[CH:8][CH:9]=2)=[CH:34][CH:35]=1)([O-:41])=[O:40]

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 178447845HCID 178447845, compound

Product 1

HCID 178447844HCID 178447844, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
65 °C

Procedure

DMSO (300 ml) and KOH (38.0 g) were added to 1,1-bis(4-hydroxyphenyl)-4-(trans-4-n-propylcyclohexyl)cyclohexane (110.6 g) obtained in the first step, followed by dissolving these together on heating to 65° C., dropwise adding to the solution, a solution of p-chloronitrobenzene (97.8 g) in DMSO (500 ml) at 65° C., reacting the mixture, aging for 5 hours, cooling down to room temperature after completion of the reaction, extracting with dichloromethane, washing with lN-NaOH aqueous solution and further with saturated NaCl aqueous solution till the aqueous solution became neutral, drying over MgSO4, treating by alumina column, distilling off the resulting eluate and recrystallizing the resulting concentrate from a mixed solvent of toluene-acetone to obtain pale yellow crystals of 1,1-bis[4-(4-nitrophenoxy)phenyl]-4-(trans-4-n-propylcyclohexyl)cyclohexane (136.1 g).

Workup

  1. customobtained in the first step
  2. dissolutionby dissolving these together
  3. additiondropwise adding to the solution
  4. customat 65° C.
  5. temperaturecooling down to room temperature
  6. customafter completion of the reaction
  7. extractionextracting with dichloromethane
  8. washwashing with lN-NaOH aqueous solution
  9. dry with materialdrying over MgSO4
  10. additiontreating by alumina column
  11. distillationdistilling off the resulting eluate and
  12. customrecrystallizing the resulting
  13. concentrationconcentrate from a mixed solvent of toluene-acetone

Sources & evidence

ORD record
ord-d21098bb0785447ca17a5d309741bb2e
Source dataset
uspto-grants-1992_10
Patent number
US05152918

Linked notes

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