2,6-Xylenol, 4-nitro- → 4-Amino-2,6-dimethylphenol

HRID 1452773Notes

Reaction equation

HRID 1452773 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]=1[OH:12].[H][H]>C(O)C.[Pd]>[NH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([OH:12])=[C:4]([CH3:11])[CH:5]=1

Participants

5

Reactant 2

HCID 170302,6-Xylenol, 4-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 826684-Amino-2,6-dimethylphenolYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1 g (6 mmole) of 2,6-dimethyl-4-nitrophenol in 20 ml of ethanol is placed under 1.5 bar of hydrogen in the presence, of 10% Pd/C for 1 hour. The Pd/C is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure. The evaporation residue crystallizes spontaneously, it is washed twice with 50 ml of heptane and dried overnight under vacuum. A cream coloured solid is obtained with a yield of 86%.

Workup

  1. filtrationThe Pd/C is eliminated by filtration on celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe evaporation residue crystallizes spontaneously
  4. washit is washed twice with 50 ml of heptane
  5. customdried overnight under vacuum
  6. customis obtained with a yield of 86%

Sources & evidence

ORD record
ord-b16b806e3ca24521b0ca0ebf57a061ef
Source dataset
uspto-grants-2009_01
Patent number
US07473779B2

Reaction notes

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