4-(2-Hydroxy-1-decyloxy)nitrobenzene → 4-(2-Hydroxy-1-decyloxy)aniline

HRID 1743091Notes

Reaction equation

HRID 1743091 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.[H][H]>C(OCC)(=O)C.[Pd]>[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 222377694-(2-Hydroxy-1-decyloxy)nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 222377714-(2-Hydroxy-1-decyloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-hydroxy-1-decyloxy)nitrobenzene (20 g, 0.68 mol) was dissolved in ethyl acetate (200 mL) and 10% palladium on carbon (2.5 g) was added to a Parr pressure bottle. The contents were then hydrogenated at 50 psi until hydrogen uptake ceased. The catalyst was removed by suction filtration through a pad of Celite. Removal of solvent afforded 4-(2-hydroxy-1-decyloxy)aniline in quantitative yield (18.0 g, 0.68 mol, 100% yield) as a tan solid.

Workup

  1. customThe catalyst was removed by suction filtration through a pad of Celite
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-67e43c96b08d480a98f74350ff1c82b4
Source dataset
uspto-grants-2006_03
Patent number
US07008759B2

Reaction notes

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