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

HRID 329190Notes

Reaction equation

HRID 329190 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=[CH:6][C:5]=1[OH:22])([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:7]=[CH:6][C:5]=1[OH:22]

Participants

5

Reactant 2

HCID 113812644-Dodecyl-2-nitrophenolHCID 178418361HCID 178418361, compound3×

Product 1

HCID 113119642-Amino-4-dodecylphenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 61.4 g. (0.2 mole) of 2-nitro-4-dodecylphenol and 1 g. of 5% of palladium on carbon slurried in 100 ml of 95% ethanol was placed in a 250 ml hydrogenation bottle. The bottle was stoppered under an atmosphere of 45 psi of hydrogen and shaken at room temperature. The hydrogen was replenished during reaction. After 4 hours the hydrogen uptake was complete. The mixture then was filtered through a sintered glass funnel and the filtrate was stripped of solvent under reduced pressure. The yield of product, 2-amino-4-dodecylphenol, was quantitative. Infrared, nuclear magnetic resonance (nmr) and gas liquid chromatography (glc) analyses confirmed its structure and purity.

Workup

  1. additionA mixture of 61.4 g
  2. filtrationThe mixture then was filtered through a sintered glass funnel

Sources & evidence

ORD record
ord-33eba2bacb0249d3a1c5779377472f08
Source dataset
uspto-grants-1977_04
Patent number
US04020081

Reaction notes

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