Phenol, 4-(1,1-dimethylethyl)-2-nitro- → 2-Amino-4-tert-butylphenol

HRID 609526Notes

Reaction equation

HRID 609526 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[OH:14])([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]([CH3:12])([CH3:11])[CH3:13])[CH:7]=[CH:6][C:5]=1[OH:14]

Participants

5

Reactant 2

HCID 18661Phenol, 4-(1,1-dimethylethyl)-2-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 709822-Amino-4-tert-butylphenolYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available 4-t-butyl phenol (30 g, 0.2 mole) was dissolved in 200 mL ethyl acetate in a 600-mL round-bottomed flask fitted with a mechanical stirrer, and cooled to 0° C. The mixture was treated with nitric acid (13 mL, in 13 mL water) dropwise over 10 min and then a catalytic amount of NaNO2. After 45 min the reaction was washed with excess 1N HCl and the organic layer was dried over MgSO4 and stripped to yield 37 g of 2-nitro-4-t-butyl phenol. This nitrophenol (37 g, 0.19 mole) was dissolved in 100 mL ethyl acetate and placed into a Parr bottle with a teaspoon of 10% Pd/C. The mixture was placed on a hydrogenator under 50 psi hydrogen with agitation for 1 hr. The catalyst was filtered off through celite, and the ethyl acetate was stripped off under vacuum. The material crystallized with the addition of about 200 mL heptane to give 25.6 g of the corresponding amine (2-amino-4-t-butyl phenol).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. customThe material crystallized with the addition of about 200 mL heptane

Sources & evidence

ORD record
ord-403eb750e145455fa6b509654d3dcc42
Source dataset
uspto-grants-1999_12
Patent number
US05998121

Reaction notes

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