4-Nitro-1,2-bis(octyloxy)benzene → HCID 14980194, compound

HRID 1353136Notes

Reaction equation

HRID 1353136 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([N+:25]([O-])=O)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[NH2:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 140913894-Nitro-1,2-bis(octyloxy)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 14980194HCID 14980194, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dioctyloxynitrobenzene (25.25 g, 0.067 mol) was dissolved in ethyl acetate (250 mL) in a Parr bottle. 10% Pd on charcoal (3.5 g) was added and the mixture was hydrogenated (5–6 hr) at 50 psi until the hydrogen uptake ceased. The reaction mixture was filtered and evaporated. The aniline was obtained as a dark syrup. (22.5 g, 0.064 mol, 97% yield).

Workup

  1. custom(5–6 hr)
  2. filtrationThe reaction mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-69af30017f9d47fc8076681a882bbe86
Source dataset
uspto-grants-2007_05
Patent number
US07220868B2

Reaction notes

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