Sodium Hydroxide → 2-Benzylpropane-1,3-diol

HRID 1939890

Reaktionsgleichung

Reaktionsgleichung von HRID 1939890
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>CCOCC>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5202412-Benzylpropane-1,3-diolAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Slowly add a solution of diethyl 2-benzylmalonate (20 g) in Et2O (300 mL) to a slurry of LiAlH4 (6 g) in Et2O (300 mL), then heat the reaction mixture at reflux for 14 h. Carefully add 4N NaOH to the reaction mixture until there is no precipitate, then extract with EtOAc. Concentrate the organic layer and purify the crude product on a silica gel column, eluting with EtOAc to obtain 2-benzyl-1,3-propanediol (8.45 g).

Aufarbeitung

  1. temperatureheat the reaction mixture
  2. temperatureat reflux for 14 h
  3. extractionextract with EtOAc
  4. concentrationConcentrate the organic layer
  5. custompurify the crude product on a silica gel column
  6. washeluting with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-88bac1799d3a4ae4a0f6d84a9b4445e2
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698548

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