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

HRID 1732847Notes

Reaction equation

HRID 1732847 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 moles) of 2-nitro-4-dodecylphenol and 1 g of 5% 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 four 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, nmr and gas liquid chromotography (glc) analyses confirmed its structure and purity.

Workup

  1. filtrationThe mixture then was filtered through a sintered glass funnel

Sources & evidence

ORD record
ord-0150d17eebf445d890a115047848248a
Source dataset
uspto-grants-1980_12
Patent number
US04239699

Reaction notes

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