Nitric Acid → 2-Nitro-4-nonylphenol

HRID 249230

Reaction equation

HRID 249230 reaction equation
[CH2:1]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C>[N+:17]([C:14]1[CH:15]=[C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:11]=[CH:12][C:13]=1[OH:16])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 17524-Nonylphenol

Product 1

HCID 181835482-Nitro-4-nonylphenolYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10 g of 4-nonylphenol (manufactured by Tokyo Kasei K.K., containing 10% of ortho compound) was dissolved in 30 ml of acetic acid and to the resulting solution was added 20 ml of 30% solution of nitric acid at 5°-10° C. for 2 hours. After 10 minutes, the resulting solution was treated with 50 g of ice water and then extracted with three 50-ml portions of ether. The ether was distilled off and then the residue was isolated using a silica gel column to obtain 9.33 g of the desired product in a 78% yield.

Workup

  1. extractionextracted with three 50-ml portions of ether
  2. distillationThe ether was distilled off
  3. customthe residue was isolated

Sources & evidence

ORD record
ord-06b804ffcfc54dfab60084ee8966f56c
Source dataset
uspto-grants-1993_05
Patent number
US05213888

Linked notes

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