Phenol, 3-(1,1-dimethylethyl)- → 2-[2-(3-Tert-butyl-phenoxy)-ethyl]-[1,3]dioxane

HRID 1879675

Reaktionsgleichung

Reaktionsgleichung von HRID 1879675
[OH-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].Br[CH2:15][CH2:16][CH:17]1[O:22][CH2:21][CH2:20][CH2:19][O:18]1>O.C(OCC)(=O)C.C(O)(=O)C>[C:3]([C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:15][CH2:16][CH:17]1[O:22][CH2:21][CH2:20][CH2:19][O:18]1)([CH3:6])([CH3:4])[CH3:5]

Komponenten

7

Edukt 3

HCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 14798Sodium HydroxideHCID 5206561,3-Dioxane, 2-(2-bromoethyl)-

Produkt 1

HCID 595485522-[2-(3-Tert-butyl-phenoxy)-ethyl]-[1,3]dioxane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Sodium hydroxide (3.46 g, 1.3 eq) was taken up in water (20 mL) and stirred for about 30 minutes. Then 3-tert-butyl phenol (10.0 g, 66.6 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. Next, 2-(2-bromoethyl)-[1,3]dioxane (9.9 mL, 1.1 eq) was added ant the resulting mixture was heated at reflux for 40 hours. The reaction mixture was cooled to room temperature and then added ethyl acetate (150 mL) and with stirring acetic acid was added to pH=4, followed by dilution with water (100 mL) and ethyl acetate (150 mL). After partitioning, the layers were separated and then washed the organic layer with water (3×100 mL) and the ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a colorless oil (16.91 g).

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. temperaturewas heated
  3. temperatureat reflux for 40 hours
  4. customAfter partitioning
  5. customthe layers were separated
  6. washwashed the organic layer with water (3×100 mL)
  7. dry with materialthe ethyl acetate layers were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-83be275999f24c53aa4056ecd01cbb9e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318719B2

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