Ammonia → 2,3,6-Trimethylcyclohexan-1-one

HRID 223606

Reaction equation

HRID 223606 reaction equation
[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH:5]=[C:4]([CH3:9])[C:3]1=[O:10].C[N:12]1CCOCC1.N>[Pd].[Zn]>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[NH2:12].[CH3:1][CH:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]([CH3:9])[C:3]1=[O:10]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 892642-Cyclohexen-1-one, 2,5,6-trimethyl-

Product 2

HCID 1425832,3,6-Trimethylcyclohexan-1-oneHCID 119589472,3,6-Trimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 23994ZincCatalyst

Procedure

In a stirred autoclave having a useful capacity of 300 parts by volume, a solution of 35 parts of 2,3,6-trimethylcyclohex-5-en-1-one in 35 parts of N-methylmorpholine, 34 parts of ammonia and 5 parts of a finely divided catalyst, containing 0.5% by weight of Pd and 0.1% by weight of Zn on Al2O3, are kept for 10 hours at 230° C. and the autogenous pressure (about 150 bar). The mixture is then allowed to cool, filtered and purified by distillation. 18.2 parts of 2,3,6-trimethylaniline and 15.3 parts of 2,3,6-trimethylcyclohexan-1-one are obtained, the latter presumably through partial hydrogenation of the 2,3,6-trimethylcyclohex-5-en-1-one starting material with the hydrogen formed during the reaction. Since 2,3,6-trimethylcyclohexan-1-one can in turn be converted to the desired 2,3,6-trimethylaniline, for example as described in Example 1 or 2, the selectivity of the reaction is 96%.

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. distillationpurified by distillation

Sources & evidence

ORD record
ord-7a776762b5914e1cb244a050d0a88372
Source dataset
uspto-grants-1982_10
Patent number
US04355180

Linked notes

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