반응 #5105

반응 방정식

hydrogen peroxide

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

9-borabicyclononane

sodium hydroxide

→

5-p-t-butylphenoxy-1-pentanol

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도at reflux for one hour
2. 2
   기타was partitioned between 150 ml ether-150 ml water
3. 3
   기타The ether layer was removed
4. 4
   건조dried (MgSO4)
5. 5
   기타evaporated to a yellow oil which
6. 6
   기타was chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
7. 7
   기타yielding a yellow oil which
8. 8
   기타distiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g

실험 절차

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.

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