Ammonia → 2-tert-Butyl-6-methylaniline

HRID 1579722Notes

Reaction equation

HRID 1579722 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1O.CC1CCCC(C(C)(C)C)C1=O.[NH3:25].C1(=O)CCCCC1>[Pd].O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1[NH2:25]

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 7967CyclohexanoneHCID 166782-tert-Butyl-6-methylphenolHCID 12400475HCID 12400475, compound

Product 1

HCID 831552-tert-Butyl-6-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×

Procedure

In a pressure reaction vessel was placed 0.55 mole parts of 2-methyl-6-tert-butylphenol, 0.55 mole parts of 2-methyl-6-tert-butylcyclohexanone, 0.0045 mole parts of palladium (5 weight per cent on charcoal support) and 3 mole parts of ammonia. The vessel was sealed and, while stirring, heated to 250°C. (Water was not added in this example because the initial reaction of ammonia with cyclohexanone produced 0.55 mole part of water.) The mixture was stirred at this temperature for 3 hours and then cooled and distilled, giving a 46.8 per cent conversion to 2-methyl-6-tert-butyl aniline. The yield of 2-methyl-6-tert-butyl aniline based on consumed phenol was about 98 per cent.

Workup

  1. customIn a pressure reaction vessel
  2. customThe vessel was sealed
  3. stirring) The mixture was stirred at this temperature for 3 hours
  4. temperaturecooled
  5. distillationdistilled

Sources & evidence

ORD record
ord-075c44150a9642f1b1a292a0cda15e22
Source dataset
uspto-grants-1976_01
Patent number
US03931298

Reaction notes

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