2,4-Dinitro-1-[4-(octyloxy)phenoxy]benzene → HCID 22665187, compound

HRID 1007738Notes

Reaction equation

HRID 1007738 reaction equation
[N+:1]([C:4]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9][CH:8]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:5]=1[O:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 226651852,4-Dinitro-1-[4-(octyloxy)phenoxy]benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22665187HCID 22665187, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The resultant 1-[4-(2,4-dinitrophenoxy)phenoxy]octane (31.08 g, 0.080 mol) and ethanol (700 ml) and 10% Pd/C (1.50 g) were introduced into a 2-liter (l) reaction bottle. After hydrogen passed through the reaction under normal pressure for 4 hours, the reaction mixture was filtered and concentrated to obtain a crude product. The crude product was recrystallized by ethanol to obtain 1-[4-(2,4-diaminophenoxy)phenoxy]octane (22.33 g, 0.068 mol). Yield: 85%. Spectrum: IR (KBr) 3420, 3352, 2924, 2856, 1618, 1503, 1466, 1215, 1105, 1027 cm−1, 1H NMR (DMSO-d6, 300 MHz). δ0.8˜6.7 (m, 4H), 6.46 (d, J=8.3 Hz, 1H), 6.02 (d, J=2.0 Hz, 1H), 5.79 (dd, J=8.5, J=2.2 Hz, 1H), 4.61 (s, 2H), 4.47 (s, 2H), 3.82 (t, J=5.7 Hz, 2H), 1.70˜1.50 (m, 2H), 1.40˜1.10 (m, 10H), 0.84 (t, J=6.1 Hz, 3H). 13C NMR (DMSO-d6, 75 MHz). δ153.5, 152.7, 151.3, 146.1, 140.9, 133.4, 121.4, 116.8, 115.3, 103.2, 101.6, 68.0, 31.5, 29.0, 28.9, 25.7, 22.3, 14.1

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated
  3. customto obtain a crude product
  4. customThe crude product was recrystallized by ethanol

Sources & evidence

ORD record
ord-59b6dc4b7f844123bee79fdae9738ef4
Source dataset
uspto-grants-2004_09
Patent number
US06797344B2

Reaction notes

Loading…