Hydrogen Peroxide → 5-p-t-Butylphenoxy-1-pentanol

HRID 5009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5009
[C:1]([C:5]1[CH:16]=[CH:15][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C2CCCCCCCC2)BCCCCCCC1.[OH-:35].[Na+].OO>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:35])=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 133137331-tert-Butyl-4-[(pent-4-en-1-yl)oxy]benzeneHCID 178418648HCID 178418648, Verbindung

Produkt 1

HCID 133137345-p-t-Butylphenoxy-1-pentanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureat reflux for one hour
  2. customwas partitioned between 150 ml ether-150 ml water
  3. customThe ether layer was removed
  4. dry with materialdried (MgSO4)
  5. customevaporated to a yellow oil which
  6. customwas chromatographed through 300 g, 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent)
  7. customyielding a yellow oil which
  8. customdistiled (126° C./0.75 mm) to a clear, colorless oil, 5-p-t-butylphenoxy-1-pentanol, 1.7 g

Quellen und Nachweise

ORD-Eintrag
ord-738ff1beafd14a068396998334793f43
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242936

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