4-Nitrobenzaldehyde → 2,6-Di-tert-butyl-4-[4-nitro-alpha-(piperidin-1-yl)benzyl]phenol

HRID 52752

Reaktionsgleichung

Reaktionsgleichung von HRID 52752
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[N+:16]([C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)([O-:18])=[O:17].[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(O)CCC>[C:11]([C:7]1[CH:8]=[C:9]([CH:23]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:22]2[CH:25]=[CH:26][C:19]([N+:16]([O-:18])=[O:17])=[CH:20][CH:21]=2)[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 5414-NitrobenzaldehydeHCID 8082PiperidineHCID 314052,6-Di-tert-butylphenol

Produkt 1

HCID 199638692,6-Di-tert-butyl-4-[4-nitro-alpha-(piperidin-1-yl)benzyl]phenolAusbeute 23,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 2.1 g (0.01 mol) of 2,6-di-tert-butylphenol, 1.51 g (0.01 mol) of 4-nitrobenzaldehyde and 0.9 g (0.0105 mol) of piperidine is refluxed under nitrogen in 15 ml n-butanol for 24 hours. The solution is then evaporated in vacuo. The residue is then chromatographed on silica gel with hexane:ethyl acetate (4:1 ). The pure fractions are recrystallized from acetonitrile to give 1.0 g of the title compound as pale yellow crystals, melting at 147° -148° C.

Aufarbeitung

  1. customThe solution is then evaporated in vacuo
  2. customThe residue is then chromatographed on silica gel with hexane:ethyl acetate (4:1 )
  3. customThe pure fractions are recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-42501c0ec9f841a0ab22c5f6bd4cd6ba
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616774

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