Ammonia → 2-tert-Butyl-6-methylaniline

Participants

Reaction Conditions

Reaction Steps

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 A sample was withdrawn and analyzed by gas chromatography at this point and found to be 72 per cent 2-methyl-6-tert-butylphenol and 20 per cent 2-methyl-6-tert-butyl cyclohexanone.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.

Provenance & Evidence