HCID 22665186, compound → HCID 22665184, compound

HRID 1007740Notes

Reaction equation

HRID 1007740 reaction equation
[N+:1]([C:4]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:5]=1[O:6][C:7]1[CH:25]=[CH:24][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:5]=1[O:6][C:7]1[CH:25]=[CH:24][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 22665186HCID 22665186, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22665184HCID 22665184, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The resultant 1-[4-(2,4-dinitrophenoxy)phenoxy]dodecane (35.58 g, 0.080 mol) and ethanol (700 ml) and 10% Pd/C (1.78 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 with ethanol to obtain 1-[4-(2,4-diaminophenoxy)phenoxy]dodecane (26.15 g, 0.068 mol). Yield: 85%. Spectrum:IR (KBr) 3412, 3333, 2923, 2850, 1614, 1515, 1462, 1366, 1219, 1084 cm−1. 1H NMR (DMSO-d6, 300 MHz). δ6.8˜6.7 (m, 4H), 6.45 (d, J=8.3, 1H), 6.02 (d, J=2.2 Hz, 1H), 5.79 (dd, J=8.4, J=2.4 Hz, 1H), 4.61 (s, 2H), 4.47 (s, 2H), 3.81 (t, J=6.3 Hz, 2H), 1.75˜1.55 (m, 2H), 1.40˜1.10 (m, 18H), 0.82 (t, J=6.3 Hz, 3H). 13C NMR (DMSO-d6, 75 MHz)δ 153.5, 152.7, 146.1, 140.9, 133.4,121.4, 116.8, 115.3, 103.2, 101.5, 68.0, 31.5, 29.2, 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 with ethanol

Sources & evidence

ORD record
ord-64e099ec09994212a2ca331d7ff6db48
Source dataset
uspto-grants-2004_09
Patent number
US06797344B2

Reaction notes

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