تفاعل #5105

معادلة التفاعل

hydrogen peroxide

5-(p-tert-butylphenoxy)-1-pentene

9-borabicyclononane

sodium hydroxide

→

5-p-t-butylphenoxy-1-pentanol

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for one hour
2. 2
   أخرىwas partitioned between 150 ml ether-150 ml water
3. 3
   أخرىThe ether layer was removed
4. 4
   تجفيفdried (MgSO4)
5. 5
   أخرىevaporated to a yellow oil which
6. 6
   أخرىwas chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
7. 7
   أخرىyielding a yellow oil which
8. 8
   أخرىdistiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g

الإجراء التجريبي

The 5-(p-tert-butylphenoxy)-1-pentene (10.5 g) was treated with 115 ml 0.5M 9-borabicyclononane in tetrahydrofuran and the reaction mixture was stirred at reflux for one hour. The solution was cooled to room temperature and treated with 25 ml 3N sodium hydroxide, then 10 ml 30% hydrogen peroxide. After the bubbling ceased the reaction mixture was partitioned between 150 ml ether-150 ml water. The ether layer was removed, dried (MgSO4), and evaporated to a yellow oil which was chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent) yielding a yellow oil which was vacuum distiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g.

المصدر