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

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence