Nitric Acid → 1,4-Bis(2-ethylhexyloxy)-2-nitrobenzene

HRID 1748927Notes

Reaction equation

HRID 1748927 reaction equation
[CH2:1]([CH:3]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([CH2:19][CH3:20])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][CH:7]=1)[CH3:2].[N+:25]([O-])([OH:27])=[O:26].O>C(Cl)(Cl)Cl>[CH2:19]([CH:14]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:13][O:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][C:10]=1[N+:25]([O-:27])=[O:26])[CH3:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 35799201,4-Bis(2-ethylhexyloxy)benzene

Product 1

HCID 896015891,4-Bis(2-ethylhexyloxy)-2-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

1,4-Bis(2-ethylhexyloxy)benzene (50.2 g, 0.150 mol) is dissolved in chloroform (150 ml) and cooled to 0° C. Nitric acid (70%, 17.0 g, 0.190 mol) is added dropwise at 0-3° C. and the reaction stirred whilst monitoring progress by HPLC. After 60 minutes, water (50 ml) is added and the organic layer separated, dried (MgSO4) and evaporated to give the title compound as a yellow oil (56.9 g, 100%). The material is used without further purification.

Workup

  1. customthe organic layer separated
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-bd3229c156e54d48bbee33e5a984c392
Source dataset
uspto-grants-2015_10
Patent number
US09152006B2

Reaction notes

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