Reaktion #5105

Reaktionsgleichung

hydrogen peroxide

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

9-borabicyclononane

sodium hydroxide

→

5-p-t-butylphenoxy-1-pentanol

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle