Acetanilide → (4-tert-Butyl-phenyl)-phenyl-amine

HRID 725734Notes

Reaction equation

HRID 725734 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)C.[C:11]([C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+]>[Cu].O>[C:5]1([NH:4][C:18]2[CH:19]=[CH:20][C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:16][CH:17]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 904AcetanilideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 775951-Bromo-4-tert-butylbenzene

Product 1

HCID 11447459(4-tert-Butyl-phenyl)-phenyl-amineYield 58.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

8.2 g (0.061 mol) of acetanilide, 19.2 g (0.090 mol) of p-tertiarybutylbromobenzene, 9.95 g (0.072 mol) of anhydrous potassium carbonate, and 0.50 g (0.008 mol) of copper powder were mixed. The reaction mixture was then allowed to undergo reaction at a temperature of 190° C. to 203° C. for 23 hours. The reaction product was then extracted with 75 ml of toluene. The insoluble contents were removed by filtration. The filtrate was then concentrated to dryness. The concentrate was then dissolved in 30 ml of isoamyl alcohol. The material was then hydrolyzed with 1.1 g of water and 7.9 g (0.12 mol) of 85% potassium hydroxide at a temperature of 125° C. The material was then subjected to steam distillation to distill off isoamyl alcohol and excess p-tertiarybutylbromobenzene. The residue was extracted with 80 ml of toluene, washed with water, and then concentrated to dryness. The concentrate was then recrystallized from 100 ml of n-hexane to obtain 8.1 g (yield: 58.9%) of N-phenyl-p-tertiarybutylaniline.

Workup

  1. customreaction at a temperature of 190° C. to 203° C. for 23 hours
  2. extractionThe reaction product was then extracted with 75 ml of toluene
  3. customThe insoluble contents were removed by filtration
  4. concentrationThe filtrate was then concentrated to dryness
  5. dissolutionThe concentrate was then dissolved in 30 ml of isoamyl alcohol
  6. customat a temperature of 125° C
  7. distillationThe material was then subjected to steam distillation
  8. distillationto distill off isoamyl alcohol and excess p-tertiarybutylbromobenzene
  9. extractionThe residue was extracted with 80 ml of toluene
  10. washwashed with water
  11. concentrationconcentrated to dryness
  12. customThe concentrate was then recrystallized from 100 ml of n-hexane

Sources & evidence

ORD record
ord-d93696164b2e479393f10519ee991a31
Source dataset
uspto-grants-1998_01
Patent number
US05707747

Reaction notes

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