Hydroquinone → 2,4-Dinitro-1-[4-(octyloxy)phenoxy]benzene

HRID 1007737Notes

Reaction equation

HRID 1007737 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1)[OH:15].C(=O)([O-])[O-].[K+].[K+].[Br-].[CH3:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CC(=O)CC>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:15][C:14]1[CH:21]=[CH:20][C:18]([O:19][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:17][CH:16]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6264DinitrofluorobenzeneHCID 11430Potassium Carbonate2×HCID 22066274HCID 22066274, compound

Product 1

HCID 226651852,4-Dinitro-1-[4-(octyloxy)phenoxy]benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

In a 500 ml 2-necked bottle equipped with a condenser tube, butanone (200 ml), and then 2,4-dinitrofluorobenzene (18.60 g, 0.100 mol), hydroquinone (11.32 g, 0.100 mol), and potassium carbonate (15.26 g, 0.110 mol) were introduced. The mixture were agitated at room temperature for 2 hours. Then, potassium carbonate (15.26 g, 0.110 mol), octane bromide (27.41 g, 0.110 mol), and butanone (20 ml) were added to the bottle. The mixture were stirred at room temperature for 6 hours. Thereafter, distilled water (300 ml) was added to the bottle, and the mixture was extracted by ethyl acetate (300 ml×3). The collected organic layers were dried by anhydrous sodium sulfate, filtered, and concentrated, and recrystallized by ethanol to obtain 1-[4-(2,4-dinitrophenoxy)phenoxy]octane (31.08 g, 0.080 mol). Yield: 80%. Spectrum: IR (KBr) 3096, 2938, 2854, 1604, 1526, 1504, 1476, 1348, 1273, 1240, 1188, 1116, 1069, 1001 cm−1. 1HNMR (DMSO-d6, 300 MHz). δ8.88 (d, J=2.8 Hz, 1H), 8.43 (dd, J=2.8, J=9.3 Hz, 1H), 7.21 (d, J=8.6 Hz, 2H), 7.10˜7.05 (m, 3H), 3.98 (t, J=6.4 Hz, 2H), 1.73 (quintet, J=6.7 Hz, 2H), 1.4˜1.2 (m, 10H), 0.87 (t, J=6.2, 3H) 13C NMR (DMSO-d6, 75 MHz). δ57.0, 156.1, 146.6, 141.0, 139.0, 129.7, 122.1, 122.0, 118.3, 116.3, 68.1, 31.5, 29.0, 28.9, 28.8, 25.7, 22.3, 14.1.

Workup

  1. customIn a 500 ml 2-necked bottle equipped with a condenser tube
  2. stirringThe mixture were stirred at room temperature for 6 hours
  3. distillationThereafter, distilled water (300 ml)
  4. additionwas added to the bottle
  5. extractionthe mixture was extracted by ethyl acetate (300 ml×3)
  6. dry with materialThe collected organic layers were dried by anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customrecrystallized by ethanol

Sources & evidence

ORD record
ord-c055b18ac06a4283a7203e96adcf89f2
Source dataset
uspto-grants-2004_09
Patent number
US06797344B2

Reaction notes

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