Hydrazine hydrate (1:1) → 4-Amino-2-tert-butyl-5-methyl-phenol

Participants

Reaction Steps

To a solution of 2-(tert-butyl)4-nitroso-5-methylphenol (47.0 g, 243 mmol) in ethanol (500 ml) was slowly added dropwise hydrazine hydrate (29.5 ml, 608 mmol) at 0° C. After completing the dropwise addition, the mixture was stirred at room temperature for 16 hours, and the solvent was removed under reduced pressure. The residue was combined with water (500 ml), and the crystals were filtered. The crystals were dissolved in ethyl acetate, washed with saturated brine, dried over sodium sulfate and purified by silica gel column chromatography on a small amount of silica gel which was eluted with ethyl acetate. After the solvent was removed under reduced pressure, the residue was suspended in hexane and the crystals were collected by filtration to obtain 39.3 g of the title compound.

Provenance & Evidence