Hydrochloric Acid → 2,6-Di-tert-butyl-4-({[dodecyl(dimethyl)silyl]methyl}sulfanyl)phenol

HRID 1488928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488928
[C:1]([C:5]1[CH:10]=[C:9]([SH:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][Si:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH3:27])[CH3:26].Cl>CN(C)C=O>[C:12]([C:7]1[CH:8]=[C:9]([S:11][CH2:24][Si:25]([CH3:26])([CH3:27])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 116904Silane, (chloromethyl)dodecyldimethyl-

Produkt 1

HCID 158723352,6-Di-tert-butyl-4-({[dodecyl(dimethyl)silyl]methyl}sulfanyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10 mmol), potassium carbonate (1.7 g, 12.3 mmol), chloromethyldodecyldimethylsilane (2.8 g, 10 mmole) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water, acidify with aqueous hydrochloric acid and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through fluorosil-Na2SO4 and evaporate to an orange semi-solid (4.0 g). Purify the product by first distilling (180°-200° C. @0.1 mm Hg) then subjecting to silica gel chromatography (CCl4) to obtain the title compound as a colorless oil which slowly crystallizes.

Aufarbeitung

  1. extractionextract with ethyl ether
  2. washWash the ethereal layer with water
  3. filtrationbrine, filter through fluorosil-Na2SO4
  4. customevaporate to an orange semi-solid (4.0 g)
  5. customPurify the product
  6. distillationby first distilling (180°-200° C. @0.1 mm Hg)

Quellen und Nachweise

ORD-Eintrag
ord-719d4126a9bc42e290472320da3868a3
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677291

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