4-Dodecyl-2-nitrophenol → 2-Amino-4-dodecylphenol

HRID 1030814Notes

Reaction equation

HRID 1030814 reaction equation
[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([N+:20]([O-])=O)[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H][H]>[Pd].O1CCCC1>[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([NH2:20])[CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 113812644-Dodecyl-2-nitrophenol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 113119642-Amino-4-dodecylphenolYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.80 g of the 4-dodecyl-2-nitrophenol obtained in (2) above was mixed with 500 mg of 5% active carbon-supported palladium, and 150 ml of tetrahydrofuran and the resulting mixture was contacted with hydrogen at room temperature for 7 hours to reduce the nitro group. The reaction mixture was filtered, and then the solvent was distilled off to obtain 5.21 g of 4-dodecyl-2-aminophenol.

Workup

  1. additionabove was mixed with 500 mg of 5% active carbon-
  2. filtrationThe reaction mixture was filtered
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2c5a3593353744a09423d7e5bec35886
Source dataset
uspto-grants-1992_04
Patent number
US05106989

Reaction notes

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