反応 #5104

反応方程式

p-tert-butylphenol

phenoxide

phenoxide

4-chlorobutyl acetate

sodium hydride

→

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

溶媒

dimethyl formamide

dimethyl formamide

dimethyl formamide

反応条件

後処理

1. 1
   その他had totally formed
2. 2
   その他The reaction mixture was partitioned between water/toluene
3. 3
   その他The organic layer was removed
4. 4
   洗浄washed with water
5. 5
   その他The organic layer was removed
6. 6
   その他dried
7. 7
   その他evaporated to an orange oil, 5.6 g
8. 8
   その他The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

実験手順

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.

出典