Butyl 3-(p-tert-butylphenoxy)-propionate → 3-p-t-Butyl-phenoxypropanol

HRID 5007

Reaktionsgleichung

Reaktionsgleichung von HRID 5007
[C:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][C:12](OCCCC)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]([C:5]1[CH:20]=[CH:19][C:8]([O:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

This ester 21.0 g was dissolved in 500 ml dry ether and cooled to -5° C. in an ice/acetone bath. To the cold solution was added, cautiously, a slurry of 3.5 g lithium aluminum hydride in 100 ml dry ether. After one hour the excess lithium aluminum hydride was destroyed by the cautious addition of 200 ml ethyl acetate, then 50 ml water. The solution was filtered and the filtrated partitioned between 200 ml ether-200 ml water. The organic layer was removed, dried, and evaporated to a yellow oil which was vacuum distilled (116° C./0.35 mm) over potassium carbonate to a clear colorless oil, 3-p-t-butylphenoxypropanol, 10.1 g (64%).

Aufarbeitung

  1. additionTo the cold solution was added
  2. customAfter one hour the excess lithium aluminum hydride was destroyed by the cautious addition of 200 ml ethyl acetate
  3. filtrationThe solution was filtered
  4. customthe filtrated partitioned between 200 ml ether-200 ml water
  5. customThe organic layer was removed
  6. customdried
  7. customevaporated to a yellow oil which
  8. distillationdistilled (116° C./0.35 mm) over potassium carbonate to a clear colorless oil, 3-p-t-butylphenoxypropanol, 10.1 g (64%)

Quellen und Nachweise

ORD-Eintrag
ord-5c7452413c6c4954b4611120e361a41f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242936

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