Ammonium Chloride → HCID 11070377, Verbindung

HRID 1452372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452372
[Li].[C:2]([O:5][C:6]1[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][C:9]([OH:18])=[C:10]([C:13]=1[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[O:12])(=[O:4])[CH3:3].Br[CH:24]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28].[Cl-].[NH4+]>O1CCCC1>[C:2]([O:5][C:6]1[C:7]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:8][C:9]([OH:18])=[C:10]([CH:11]([OH:12])[CH:24]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34])[C:13]=1[C:14]([CH3:15])([CH3:17])[CH3:16])(=[O:4])[CH3:3]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 110445455-Acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehydeHCID 22918674HCID 22918674, Verbindung

Produkt 1

HCID 11070377HCID 11070377, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium (2.8 g) was added to a solution of 5-acetoxy-4,6-di-tert-butyl-2-hydroxybenzaldehyde (24.3 g) and 5-bromo-2,8-dimethylnonane (47.0 g) in tetrahydrofuran (200 ml) under ice cooling under a nitrogen atmosphere and the mixture was stirred overnight. The reaction mixture was poured into ice water, neutralized with a saturated aqueous solution of ammonium chloride and subjected to extraction with diethyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-2-(2,2-diisoamyl-1-hydroxyethyl)phenol [17.0 g (yield, 46%)] as a colorless oil.

Aufarbeitung

  1. extractionsubjected to extraction with diethyl ether
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6cf953d44fc64bf7804b90705ea53884
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05606089

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