4-tert-Butylphenol → 4-(4-Tert-butylphenoxy)butyl acetate

HRID 544594

Reaktionsgleichung

Reaktionsgleichung von HRID 544594
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[O-]C1C=CC=CC=1.[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28]Cl)(=[O:23])[CH3:22]>CN(C)C=O>[C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[CH:12][CH:11]=1)(=[O:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 73934-tert-ButylphenolHCID 233991-Butanol, 4-chloro-, 1-acetateHCID 24758Sodium hydrideHCID 119047Phenolate2×

Produkt 1

HCID 133137364-(4-Tert-butylphenoxy)butyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, dropwise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1 N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate.

Aufarbeitung

  1. customhad totally formed
  2. customThe reaction mixture was partitioned between water/toluene
  3. customThe organic layer was removed
  4. washwashed with water
  5. customThe organic layer was removed
  6. customdried
  7. customevaporated to an orange oil, 5.6 g
  8. customThe oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

Quellen und Nachweise

ORD-Eintrag
ord-68859b502a7640898737464c79dba6be
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04451474

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