Ammonia → 2-tert-Butyl-6-methylaniline

HRID 1579723Notes

Reaction equation

HRID 1579723 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.[NH3:13].[OH-].[NH4+].[H][H]>[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]=1[NH2:13]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 166782-tert-Butyl-6-methylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 831552-tert-Butyl-6-methylaniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
200 °C

Procedure

In a pressure reaction vessel was placed one mole part of 2-methyl-6-tert-butylphenol and 0.0045 mole part of palladium (5 weight per cent palladium on charcoal). Then, 3 mole parts of ammonia were added as 29 per cent aqueous ammonium hydroxide. The vessel was sealed and pressurized with hydrogen to 1,000 psig and heated to 200°C. Hydrogenation was continued until a total pressure drop of 820 psi was obtained. A sample was withdrawn and analyzed by gas chromatography at this point and found to be 72 per cent 2-methyl-6-tert-butylphenol and 20 per cent 2-methyl-6-tert-butyl cyclohexanone. The sealed vessel was then heated to 250°C and stirred at this temperature for 15 hours. The vessel was cooled and the contents distilled to give a 52.4 per cent conversion and 95.8 per cent yield of 2-methyl-6-tert-butyl aniline.

Workup

  1. customIn a pressure reaction vessel
  2. customThe vessel was sealed
  3. customwas obtained
  4. customA sample was withdrawn
  5. temperatureThe sealed vessel was then heated to 250°C
  6. temperatureThe vessel was cooled
  7. distillationthe contents distilled

Sources & evidence

ORD record
ord-3130057ea21b40faab0b02354c99007b
Source dataset
uspto-grants-1976_01
Patent number
US03931298

Reaction notes

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