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

HRID 1719876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719876
[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 0.5 M 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 3 N 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 ws 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 distilled (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 ws 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. distillationdistilled (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-88bb89b2e47545ba958f918de5d8f738
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04543362

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