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

HRID 2104291Notes

Reaction equation

HRID 2104291 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 mmol) 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-dbd1b5d03552442a8d2a409e291238a3
Source dataset
uspto-grants-2009_08
Patent number
US07576241B2

Reaction notes

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