Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 2309681

Reaktionsgleichung

Reaktionsgleichung von HRID 2309681
[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.[Al].[Li].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[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 69090Diethyl 2-benzylpropanedioateHCID 16211445Aluminum;lithiumHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5202412-Benzylpropane-1,3-diolAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of diethyl benzylmalonate (107 g, 0.43 mol) in 300 ml dry diethyl ether was added under nitrogen to a suspension of 24.5 g (0.65 mol) lithium aluminium hudride (LiAlH4) in 220 ml dry ether so to maintain a gentle reflux. The reaction mixture was refluxed for 2 more hours after the addition was completed. The excess of LiAlH4 was destroyed by addition of 50 ml ethyl acetate, followed by 50 ml water and finally by 600 ml 15% sulfuric acid. The ether phase was extracted by a saturated sodium bicarbonate solution and a saturated sodium chloride solution and dried over magnesium sulfate. Evaporation of the solvent left a white solid that was purified by recrystallization in ether. An amount of 45.8 g (0.28 mol) of 2-benzyl-1,3-propanediol was obtained (yield=64%).

Aufarbeitung

  1. temperatureto maintain a gentle reflux
  2. temperatureThe reaction mixture was refluxed for 2 more hours
  3. additionafter the addition
  4. customThe excess of LiAlH4 was destroyed by addition of 50 ml ethyl acetate
  5. extractionThe ether phase was extracted by a saturated sodium bicarbonate solution
  6. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  7. customEvaporation of the solvent
  8. waitleft a white solid
  9. customthat was purified by recrystallization in ether

Quellen und Nachweise

ORD-Eintrag
ord-d52789de329743cb8852a6a731775ce2
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04696920

Verknüpfte Notizen

Wird geladen…