Reacción #40294

Ecuación de reacción

1-nitro-4-tert-butyl-2,6-dimethylbenzene

1-nitro-4-tert-butyl-2,6-dimethylbenzene

CaCl2

→

brown oil

Rendimiento 93.2%

2,6-dimethyl-4-tert-butylaniline

Rendimiento 93.2%

Disolventes

ethanol

Water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled to ambient temperature
2. 2
   Filtraciónfiltered
3. 3
   ExtracciónThe filtrate was extracted three times with ether
4. 4
   Secadothe organic layer was dried over MgSO4
5. 5
   OtroRemoval of the solvent

Procedimiento

Water, 20 mL, was added to a mixture of 12.0 g (58.0 mmol) of 1-nitro-4-tert-butyl-2,6-dimethylbenzene dissolved in 160 mL of ethanol. To the stirring solution of 1-nitro-4-tert-butyl-2,6-dimethylbenzene was added CaCl2, 4.8 g (43.2 mmol), dissolved in 20 mL of water, followed by the addition of zinc powder, 50.0 g (76.5 mmol). The reaction was stirred overnight at 65° C., then cooled to ambient temperature and filtered. The filtrate was extracted three times with ether, and the organic layer was dried over MgSO4. Removal of the solvent gave 9.58 g (93%) of a brown oil. 1H NMR (300 MHz, CDCl3): δ=6.90, s, 2H; 3.40, broad singlet, 2H; 2.11, s, 6H, 1.21, s, 9H.

Fuente