Hydroquinone → HCID 22665186, compound

HRID 1007739Notes

Reaction equation

HRID 1007739 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][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>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][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])=[CH:17][CH:16]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6264DinitrofluorobenzeneHCID 11430Potassium Carbonate2×HCID 21988968HCID 21988968, compound

Product 1

HCID 22665186HCID 22665186, compoundYield 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 (18.61 g, 0.100 mol), hydroquinone (11.33 g, 0.100 mol), and potassium carbonate (15.28 g, 0.110 mol) were introduced. The mixture were agitated at room temperature for 2 hours. Then, potassium carbonate (15.27 g, 0.110 mol), dodecane bromide (15.26 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]dodecane (35.58 g, 0.080 mol). Yield: 80%. Spectrum: IR (KBr) 3121,3088, 2918, 2853, 1611, 1530, 1470, 1350, 1287, 1159, 1097, 1075 cm−1. 1H NMR (DMSO-d6, 300 MHz). δ8.84 (d, J=2.5 Hz, 1H), 8.40 (dd, J=2.5, J=9.3 Hz, 1H), 7.17 (d, J=8.9 Hz, 2H), 7.03 (t, J=9.9 Hz, 3H), 3.94 (t, J=6.4 Hz, 2H), 1.70 (quintet, J=6.8 Hz, 2H), 1.4˜1.2 (m, 18H), 0.83 (t, J=6.0, 3H) 13C NMR (DMSO-d6, 75 MHz) δ157.0, 156.1, 146.5, 141.0, 139.0, 129.6, 121.9, 118.3, 116.2, 68.2, 68.1, 31.5, 29.2, 29.0, 28.9, 25.7, 22.3, 14.0.

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-1c25799927244a2f8046768a62776ecc
Source dataset
uspto-grants-2004_09
Patent number
US06797344B2

Reaction notes

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