1-Nitro-4-tert-butyl-2,6-dimethylbenzene → 4-Tert-butyl-2,6-dimethylaniline

HRID 1759452Notes

Reaction equation

HRID 1759452 reaction equation
[N+:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][C:5]=1[CH3:15])([O-])=O>[Pd].C(O)C>[CH3:15][C:5]1[CH:6]=[C:7]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:8]=[C:9]([CH3:10])[C:4]=1[NH2:1]

Participants

4

Reactant 1

HCID 2233901-Nitro-4-tert-butyl-2,6-dimethylbenzene

Product 1

HCID 12296974-Tert-butyl-2,6-dimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 1 liter stirred autoclave were charged 62 g. (0.3 mole) of 2-nitro-1,3-dimethyl-5-tertiary-butyl-benzene, 300 ml. of ethanol and 1.0 g. of 5% palladium on charcoal. The autoclave was purged with hydrogen and then pressure to 1000 psig at 90° C. to 95° C. After 1 hour, the reaction was stopped. A total of 500 psig were taken up. The reaction mixture was filtered through Celite and the ethanol was evaporated. The final product was distilled at 93° C. to 98° C./7 to 10 torr to yield 47.2 g. of a very pale yellow liquid. An 89% isolated yield of 99+% pure 2,6-dimethyl-4-tertiary-butylaniline was obtained.

Workup

  1. additionwere charged 62 g
  2. customThe autoclave was purged with hydrogen
  3. customat 90° C. to 95° C
  4. filtrationThe reaction mixture was filtered through Celite
  5. customthe ethanol was evaporated
  6. distillationThe final product was distilled at 93° C. to 98° C./7 to 10 torr
  7. customto yield 47.2 g

Sources & evidence

ORD record
ord-1eae9fdaadaa46f7a91def20e14a0b01
Source dataset
uspto-grants-1982_07
Patent number
US04340758

Reaction notes

Loading…