Tetrahydrofuran → 2-Amino-4,5-dimethylphenol

HRID 377937Notes

Reaction equation

HRID 377937 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.O1CCCC1>[Pd].C(O)C>[CH3:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([NH2:10])=[C:5]([OH:9])[CH:6]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 3491174,5-Dimethyl-2-nitrophenol

Product 1

HCID 810992-Amino-4,5-dimethylphenolYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 4,5-dimethyl-2-nitrophenol(11.7 g, 0.07 mol), tetrahydrofuran(100 ml) and ethanol(40 ml) were added, and 10% palladium/activated carbon(0.57 g) was added slowly, and then the mixture was hydrogenated for 5 hours. The reaction mixture was concentrated and chromatographed by the same way above to obtain the titled compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customchromatographed by the same way above

Sources & evidence

ORD record
ord-3f2a1a0f09fe486b9818395566adab45
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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