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3-Chloro-2-methyl-1-propene → HCID 11726907, Verbindung

HRID 1900499
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1900499
[H-].[Na+].[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:11][C:10]([OH:17])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4].Cl[CH2:23][C:24]([CH3:26])=[CH2:25].[Cl-].[NH4+]>CN(C)C=O>[C:3]([O:6][C:7]1[C:12]([C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:11][C:10]([O:17][CH2:25][C:24]([CH3:26])=[CH2:23])=[CH:9][C:8]=1[C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:5])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 111399982,6-DI-Tert-butyl-4-hydroxyphenyl acetate

Produkt 1

HCID 11726907HCID 11726907, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Versuchsvorschrift

60% Oily sodium hydride (0.18 g) was suspended in N,N-dimethylformamide (10 ml). A solution of 4-acetoxy-3,5-di-tert-butylphenol (1 g) in N,N-dimethylformamide (5 ml) was added dropwise to the suspension under ice cooling and the mixture was stirred for 30 min. Subsequently, the reaction mixture was allowed to warm to room temperature and 3-chloro-2-methyl-1-propene (0.45 ml) was added dropwise. After stirring at room temperature for 2 h, a saturated aqueous solution of ammonium chloride (15 ml) was added to the reaction mixture. The mixture was subjected to extraction with diethyl ether and the organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4-acetoxy-3,5-di-tert-butyl-1-(2-methyl-2-propenyloxy)benzene [1.08 g (yield, 90%)] as a colorless liquid.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 2 h
  2. extractionThe mixture was subjected to extraction with diethyl ether
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bdc83440170f4d50a4c06be6aa908655
Quelldatensatz
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05574178

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