Reaktion #5104

Reaktionsgleichung

p-tert-butylphenol

phenoxide

phenoxide

4-chlorobutyl acetate

sodium hydride

→

4-(p-tert-butylphenoxy)-butyl acetate

Lösungsmittel

dimethyl formamide

dimethyl formamide

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, drop-wise, 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 1N 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.

Quelle