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

HRID 985582

Reaction equation

HRID 985582 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([N:11]=O)[C:8]([CH3:13])=[CH:7][C:6]=1[OH:14])([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[NH2:11][C:9]1[C:8]([CH3:13])=[CH:7][C:6]([OH:14])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2285202-Tert-butyl-5-methyl-4-nitrosophenol

Product 1

HCID 4251824-Amino-2-tert-butyl-5-methyl-phenolYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  1. additionthe dropwise addition
  2. customthe solvent was removed under reduced pressure
  3. filtrationthe crystals were filtered
  4. dissolutionThe crystals were dissolved in ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. custompurified by silica gel column chromatography on a small amount of silica gel which
  8. washwas eluted with ethyl acetate
  9. customAfter the solvent was removed under reduced pressure
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-dd1228a10cc24116912b967593a1fa79
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Linked notes

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