تفاعل #5104

معادلة التفاعل

p-tert-butylphenol

phenoxide

phenoxide

4-chlorobutyl acetate

sodium hydride

→

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

المذيبات

dimethyl formamide

dimethyl formamide

dimethyl formamide

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر