HCID 19389161, compound → HCID 19388958, compound

HRID 1110294Notes

Reaction equation

HRID 1110294 reaction equation
[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([N+:37]([O-])=O)[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[H][H]>[Pd].C1COCC1.C(OCC)(=O)C>[CH2:1]([O:15][C:16]1[CH:17]=[C:18]([NH2:37])[CH:19]=[CH:20][C:21]=1[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 2

HCID 19389161HCID 19389161, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19388958HCID 19388958, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.5 g of 3,4-bis(tetradecyloxy)nitrobenzene and 0.5 g of 10% palladium on carbon in 80 ml of THF and 40 ml of ethyl acetate was stirred in a hydrogen atmosphere for 4 hours when uptake ceased. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from ethyl acetate-hexane to give 2.9 g (88% yield, mp 55°-58°) of 3,4-bis(tetradecyloxy)benzenamine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-145e87b0fea142c394da38e3ea279100
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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